Supporting Information. Microwave-assisted construction of triazole-linked amino acid - glucoside conjugates as novel PTP1B inhibitors
|
|
- Ἄγγελος Λαμπρόπουλος
- 5 χρόνια πριν
- Προβολές:
Transcript
1 Supporting Information Microwave-assisted construction of triazole-linked amino acid - glucoside conjugates as novel PTP1B inhibitors Xiao-Peng He, abd Cui Li, d Xiao-Ping Jin, b Zhuo Song, b Hai-Lin Zhang, b Cheng-Jiang Zhu, ab Qiang Shen, c Wei Zhang, c Li Sheng, c Xiao-Xin Shi, d Yun Tang, d Jia Li, c * Guo-Rong Chen b * and Juan Xie a * a PPSM, Institut d Alembert, ENS de Cachan, CNRS UMR 8531, 61 Avenue du P t Wilson, F Cachan (France). joanne.xie@ens-cachan.fr; Fax: ; Tel: b Key Laboratory for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, 130 Meilong Road, Shanghai , P. R. China. mrs_guorongchen@ecust.edu.cn; Fax: ; Tel: c National Center for Drug Screening, State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai , P. R. China. jli@mail.shcnc.ac.cn; Fax: ; Tel: d School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai , P. R. China General procedure for the O-propargylation. To a solution of alcohol in anhydrous DMF at 0 C, NaH (3-5 equiv) was added. After 20 min stirring, propargyl bromide (3-5 equiv) was slowly added. After 20 min, the reaction mixture was warmed to rt and stirred for another 12 h. After which, DMF was evaporated and the resulting residue was diluted with EtOAc, washed successively with water and brine, dried over MgSO 4, filtered and concentrated to give a crude product which was purified by column chromatography. 3,4-di-O-benzyl-2,6-di-O-propargyl-α-D-glucopyranoside (8). From compound 6 (245.5 mg, 0.66 mmol), column chromatography (petroleum ether/etoac, 4:1) afforded 8 as a yellow-brown syrup (267.2 mg, 90.5 %). R f = 0.70 (petroleum ether/etoac, 1:1). [α] D = (c = 0.1/CH 2 Cl 2 ). 1 H NMR (400 MHz, CDCl 3 ) δ (m, 10H), 4.96 (d, 1H, J = 10.8 Hz), 4.78 (d, 1H, J = 12.4 Hz), 4.66 (t, 2H, J = 12.4 Hz), (m, 5H), 3.88 (t, 1H, J = 9.6 Hz), 3.83 (dd, 1H, J = 3.6, 10.4 Hz), (m, 1H), 3.65 (dd, 1H, J = 2.0, 10.4 Hz), 3.56 (t, 1H, J = 9.6 Hz), 3.49 (dd, 1H, J = 3.6, 9.6 Hz), 3.34 (s, 3H), 2.45 (t, 1H, J = 2.4 Hz), 2.38 (t, 1H, J = 2.4 Hz). 13 C NMR (100 MHz, CDCl 3 ) δ 138.4, 138.1, 128.5, 128.4, 128.3, 128.2, 128.0, 127.8, 98.1, 81.7, 80.4, 79.6, 79.5, 76.9, 75.2, 75.1, 74.3, 73.4, 69.7, 68.0, 60.5, 58.6, HR-ESI-MS m/z: calcd for C 27 H 30 O 6 +Na , found ,3-di-O-benzyl-4,6-di-O-propargyl-α-D-glucopyranoside (9). From 7 (466.8 mg, 1.20 mmol), column chromatography (petroleum ether/etoac, 15:1 to 10:1) afforded 9 as a yellow-brown syrup (468.7 mg, 84.0 %). R f = 0.65 (petroleum ether/etoac, 3:1). [α] D = (c = 1.2/CH 2 Cl 2 ). 1 H NMR (400 MHz, CDCl 3 ) δ (m, 10H), 4.96 (d, 1H, J = 10.8 Hz), 4.82 (d, 1H, J = 10.8 Hz), 4.78 (d, 1H, J = 12.0 Hz), 4.64 (d, 1H, J = 12.0 Hz), 4.59 (d, 1H, J = 3.2 Hz), (m, 2H), (m, 2H), 3.94 (t, 1H, J = 9.2 Hz), 3.83 (dd, 1H, J = 4.0, 10.4 Hz), (m, 2H), (m, 2H), 3.38 (s, 3H), (m, 2H). 13 C NMR (100 MHz, CDCl 3 ) δ 138.6, 138.0, 128.5, 128.4, 128.2, 128.1, 128.0, 127.0, 98.2, 81.8, 80.1, 79.6, 79.3, 77.0, 75.8, 75.0, 74.3, 73.4, 69.5, 68.1, 60.1, 58.6, HR-ESI-MS m/z: calcd for C 27 H 30 O 6 +K , found
2 2,6-di-O-tert-butyldimethylsilyl-3,4-di-O-propargyl-α-D-glucopyranoside (26). From compound 25 (422 mg, 1 mmol), column chromatography (EtOAc/petroleum ether, 1:10) afforded 26 as a yellow syrup (368 mg, 74 %). R f = 0.71 (EtOAc/cyclohexane, 1:10). [α] D = (c = 3.5/CH 2 Cl 2 ). 1 H NMR (300 MHz, CDCl 3 ) δ 4.91 (d, 1H, J = 3.7 Hz), (m, 4H), (m, 2H), 3.52 (m, 2H), 3.38 (m, 1H), 3.36 (s, 3H), 3.22 (t, 1H, J = 9.3 Hz), 2.44 (m, 2H), 0.85 (m, 18H), 0.06 (m, 12H). 13 C NMR (75 MHz, CDCl 3 ) δ 97.4, 80.1, 79.9, 79.8, 78.6, 74.5, 74.0, 73.5, 70.8, 62.4, 59.9, 58.3, 54.5, 25.9, 25.8, 25.7, 18.2, 17.9, -4.2, -4.5, -5.2, -5.4, General Procedure for the desilylation and O-benzylation. To a solution of silylated compound in MeOH, AcCl (0.5 equiv) was added dropwise. After over night stirring at rt, the mixture was then evaporated, dissolved in CH 2 Cl 2, then washed with NaHCO 3 sat. and brine. The organic layer was dried over MgSO 4, filtered, and evaporated to give a crude product which was directly used for the O-benzylation. To a solution of alcohol in anhydrous DMF at 0 C, NaH (5 equiv) was added. After 20 min stirring, BnBr (5 equiv) was carefully added. After 20 min, the reaction mixture was warmed to rt and stirred for another 12 h. After which, DMF was evaporated and the resulting residue was diluted with EtOAc, washed successively with water and brine, dried over MgSO 4, filtered and concentrated to give the crude product which was purified by column chromatography. 4,6-di-O-benzyl-2,3-di-O-propargyl-α-D-glucopyranoside (11). To a solution of 10 (306 mg, 0.82 mmol) in CH 2 Cl 2, TFA (0.45 ml, 5.74 mmol) was added. After stirring for 5h at rt, the mixture was neutralized with NaHCO 3, extracted with CH 2 Cl 2. The organic layer was washed with brine, dried over MgSO 4 and concentrated in vacuum to give the crude product which was used directly to the O-benzylation according to the General procedure. Purification by column chromatography (petroleum ether/etoac, 15:1 to 10:1) afforded 11 as a yellow-brown syrup (491 mg, 70.4 % for 2 steps). R f = 0.56 (petroleum ether/etoac, 3:1). [α] D = (c = 1.2/CH 2 Cl 2 ). 1 H NMR (400 MHz, CDCl 3 ) δ (m, 10H), 4.94 (d, 1H, J = 3.2 Hz), 4.91 (d, 1H, J = 11.2 Hz), 4.65 (d, 1H, J = 12.0 Hz), (m, 6H), 3.87 (t, 1H, 9.2 Hz), (m, 5H), 3.42 (s, 3H), 2.47 (t, 1H, J = 2.0 Hz), 2.44 (t, 1H, J = 2.0 Hz). 13 C NMR (100 MHz, CDCl 3 ) δ 138.1, 137.9, 128.4, 128.3, 128.2, 128.0, 127.8, 98.0, 81.6, 80.2, 79.8, 79.3, 77.3, 75.2, 75.0, 74.3, 73.5, 70.0, 68.3, 60.4, 58.7, HR-ESI-MS m/z: calcd for C 27 H 30 O 6 +Na , found ,6-di-O-benzyl-3,4-di-O-propargyl-α-D-glucopyranoside (27). Compound 26 (553 mg, 1.11 mmol) was desilylated and benzylated according to the General procedures. Column chromatography (petroleum ether/etoac, 20:1) afforded 27 as a yellow-brown syrup (374.8 mg, 75.0 % for 2 steps). R f = 0.45 (petroleum ether/etoac, 4:1). [α] D = (c = 0.1/CH 2 Cl 2 ). 1 H NMR (400 MHz, CDCl 3 ) δ (m, 10H), 4.94 (d, 1H, J = 3.6 Hz), 4.88 (d, 1H, J = 11.2 Hz), 4.79 (d, 1H, J = 10.8 Hz), 4.65 (d, 1H, J = 12.0 Hz), 4.57 (d, 1H, J = 12.0 Hz), (m, 3H), 4.23 (dd, 1H, J = 2.0, 13.2 Hz), 3.92 (t, 1H, J = 9.2 Hz), (m, 3H), 3.66 (dd, 1H, J = 3.6 Hz, 6.0 Hz), 3.56 (t, 1H, J = 9.2 Hz), 3.44 (s, 3H), 2.44 (brs, 1H), 2.40 (brs, 1H). 13 C NMR (100 MHz, CDCl 3 ) δ 138.5, 138.0, 128.5, 128.4, 128.2, 128.2, 128.4, 128.0, 127.8, 127.7, 98.1, 81.8, 80.0, 79.9, 79.4, 77.4, 75.7, 75.0, 74.4, 73.5, 69.8, 68.7, 60.0, 58.8, HR-ESI-MS m/z: calcd for C 27 H 30 O 6 +K , found General procedure for the saponification. To a solution of methyl ester in MeOH (5 ml) and water (5 ml) were added LiOH (1.5 equiv./ester). The mixture was stirred at rt for 3-12 h, then acidified with resin H +, filtered and evaporated to give the free acid. If the residue was chromatographically not uniform, it was purified by column chromatography. 3-Phenyl-2(S)-[4-(methyl 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yloxy)-methyl-1H-1,2,3-triazole-1-yl]propanoic acid (4). From compound 2 (250.0 mg, 0.35 mmol), column chromatography (EtOAc/EtOH = 5:1) afforded 4 as a white solid (194.1 mg, 79.2 %). R f = 0.67 (EtOAc/EtOH = 3:1). [α] D = (c = 0.3/MeOH). 1 H NMR (400 MHz, DMSO-d 6 ) δ 8.04 (s, 1H), (m, 15H), (m, 5H), 5.58 (brs, 1H), 4.85 (d, 1H, J = 11.2 Hz), (m, 1H), 4.72 (d, 2H, J = 11.6 Hz), 4.66 (brs, 2H), (m, 3H), 3.78 (t, 1H, J = 9.2 Hz), (m, 7H), 3.31 (s, 3H). 13 C NMR (100 MHz, DMSO-d6) δ 170.8, 142.7, 138.7, 138.4, 138.3, 137.9, 128.6, 128.2, 128.1, 128.0, 127.7, 127.6, 127.5, 127.4, 127.3, 126.2, 123.6, 96.7, 81.0, 79.5, 77.4, 74.4, 74.0, 71.3, 69.6, 68.5, 66.6, 63.9, 54.5, HR-ESI-MS m/z: calcd for C 40 H 43 N 3 O 8 +H , found p-Hydroxyphenyl-2(S)-[4-(methyl 2
3 2,3,4-tri-O-benzyl-α-D-glucopyranosid-6-yloxy)-methyl-1H-1,2,3-triazole-1-yl]propanoic acid (5). From compound 3 (120.0 mg, 0.17 mmol), column chromatography (EtOAc/EtOH = 5:1) afforded 5 as a white solid (88.3 mg, 75.0 %). R f = 0.4 (EtOAc/EtOH = 3:1). [α] D = (c = 0.3/MeOH). 1 H NMR (400 MHz, DMSO-d 6 ) δ 7.98 (s, 1H), (m, 15H), 6.85 (d, 2H, J = 8.0 Hz), (m, 2H), (m, 1H), 4.84 (d, 1H, J = 11.6 Hz), 4.81 (d, 1H, J = 3.6 Hz), (m, 2H), 4.65 (brs, 2H), 4.57 (d, 1H, J = 11.2 Hz), 4.51 (d, 1H, J = 12.4 Hz), 4.48 (d, 1H, J = 12.4 Hz), 3.79 (t, 1H, J = 9.2 Hz), (m, 5H), 3.31 (s, 3H), (m, 2H). 13 C NMR (100 MHz, DMSO-d6) δ 170.9, 155.8, 138.7, 138.5, 138.3, 129.6, 128.2, 128.1, 127.7, 127.7, 127.6, 127.6, 127.5, 127.3, 123.6, 114.9, 96.8, 81.1, 79.5, 77.4, 74.4, 74.1, 71.4, 69.7, 68.5, 66.6, 63.9, 54.5, HR-ESI-MS m/z: calcd for C 40 H 43 N 3 O 9 +H , found ,4-di-O-benzyl-2,6-di-O-{1-[(1(S)-carboxy-2-phenylethyl)]-4-methyl-1H-1,2,3-triazole-4-yl}-α-D-g lucopyranoside (14). From compound 12 (86.0 mg, 0.10 mmol), column chromatography (EtOAc/EtOH, 1:1) afforded 14 as a white solid (67.0 mg, 80.7 %). R f = 0.50 (CH 2 Cl 2 /MeOH, 1:1). [α] D = (c = 0.1/MeOH). 1 H NMR (400 MHz, DMSO-d6) δ (m, 2H), (m, 10H), (m, 10H), (m, 2H), (m, 1H), (m, 3H), (m, 2H), (m, 2H), 4.43 (d, 1H, J = 12.0 Hz), 3.76 (t, 1H, J = 8.8 Hz), (m, 6H), 3.29 (s, 3H), (m, 3H). 13 C NMR (100 MHz, DMSO-d6) δ 171.5, 171.4, 143.3, 143.2, 142.7, 142.6, 138.5, 138.0, 128.6, 128.5, 128.3, 128.2, 128.1, 128.0, , 127.6, 127.4, 126.2, 123.5, 123.2, 96.9, 81.0, 79.3, 77.0, 73.9, 71.5, 69.6, 68.5, 66.6, 65.1, 63.9, 62.8, 54.9, HR-ESI-MS m/z: calcd for C 45 H 48 N 6 O 10 -H , found ,4-di-O-benzyl-2,6-di-O-{1-[(1(S)-carboxy-2-p-hydroxyphenylethyl)]-4-methyl-1H-1,2,3-triazole-4 -yl}-α-d-glucopyranoside (15). From compound 13 (92.0 mg, 0.10 mmol), column chromatography (EtOAc/EtOH, 1:2) afforded 15 as a white solid, (74.0 mg, 87.1 %). R f = 0.34 (EtOAc/EtOH, 6:1). [α] D = (c = 0.1/MeOH). 1 H NMR (400 MHz, DMSO-d6) δ (m, 2H), (m, 10H), (m, 4H), (m, 4H), 5.08 (brs, 2H), (m, 1H), (m, 5H), (m, 2H), 4.42 (d, 1H, J = 12.0 Hz), 3.75 (t, 1H, J = 9.2 Hz) (m, 6H), 3.29 (s, 3H), (m, 3H). 13 C NMR (100 MHz, DMSO-d6) δ 171.3, 155.9, 155.8, 143.1, 142.6, 138.5, 129.5, 129.4, 128.3, 128.2, 128.0, 127.9, 127.9, 127.7, 127.6, 127.5, 123.4, 123.0, 114.9, 96.9, 81.1, 79.4, 77.0, 74.0, 71.6, 69.6, 68.5, 67.3, 66.0, 65.0, 64.0, 54.5, HR-ESI-MS m/z: calcd for C 45 H 48 N 6 O 12 +H , found ,3-di-O-benzyl-4,6-di-O-{1-[(1(S)-carboxy-2-phenylethyl)]-4-methyl-1H-1,2,3-triazole-4-yl}-α-D-g lucopyranoside (19). From compound 17 (128.9 mg, 0.15 mmol), column chromatography (EtOAc/EtOH, 1:1) afforded 19 as a white solid (124.3 mg, 99.6 %). R f = 0.28 (EtOAc/EtOH, 1:1). [α] D = (c = 0.8/MeOH). 1 H NMR (400 MHz, DMSO-d6) δ (m, 2H), (m, 10H), (m, 10H), (m, 2H), (m, 3H), (m, 5H), (m, 1H), (m, 4H), (m, 9H); 13 C NMR (100 MHz, CD 3 OD) 171.4, 138.5, 137.9, 135.9, 135.2, 128.4, 128.0, 127.9, 127.8, 127.7, 127.6, 127.6, 127.5, 127.3, 127.0, 126.5, 97.4, 81.3, 79.7, 77.2, 74.9, 73.9, 72.3, 69.7, 68.4, 66.7, 60.6, 59.9, 54.0, HR-ESI-MS m/z: calcd for C 45 H 48 N 6 O 10 -H , found ,3-di-O-benzyl-4,6-di-O-{1-[(1(S)-carboxy-2-p-hydroxyphenylethyl)]-4-methyl-1H-1,2,3-triazole-4 -yl}-α-d-glucopyranoside (20). From compound 18 (131.2 mg, 0.15 mmol), column chromatography (EtOAc/EtOH, 1:1) afforded 20 as a white solid (125.9 mg, 99.0 %). R f = 0.19 (EtOAc/EtOH, 1:1). [α] D = (c = 0.6/MeOH). 1 H NMR (400 MHz, DMSO-d6) δ 8.07 (s, 1H), 8.04 (s, 1H), (m, 10H), (m, 4H), (m, 4H), (m, 2H), (m, 4H), 4.65 (brs, 2H), 4.62 (d, 1H, J = 11.6 Hz), (m, 2H), (m, 2H), (m, 5H), (m, 3H), 3.29 (s, 3H). 13 C NMR (100 MHz, CD 3 OD) δ 171.5, 169.6, 157.0, 144.0, 143.8, 138.5, 138.0, 129.5, 127.9, 127.8, 127.6, , , 127.4, 127.1, 126.1, 124.2, 124.1, 123.9, 114.8, 114.7, 97.4, 81.3, 79.9, 77.2, 74.9, 72.5, 69.7, 68.4, 66.7, 64.9, 64.3, 63.5, 54.0, 36.7, HR-ESI-MS m/z: calcd for C 45 H 48 N 6 O 12 +Na , found ,6-di-O-benzyl-2,3-di-O-{1-[(1(S)-carboxy-2-phenylethyl)]-4-methyl-1H-1,2,3-triazole-4-yl}-α-D-g lucopyranoside (23). From compound 21 (128.9 mg, 0.15 mmol), column chromatography (EtOAc/EtOH, 1:1) afforded 23 as a white solid (124.2 mg, 99.5 %). R f = 0.23 (EtOAc/EtOH, 1:1). [α] D 3
4 = (c = 0.7/MeOH). 1 H NMR (400 MHz, DMSO-d6) δ (m, 2H), (m, 20H), 5.65 (brs, 2H), (m, 3H), (m, 3H), (m, 3H), (m, 2H), (m, 5H), (m, 3H), (m, 3H). 13 C NMR (100 MHz, CD 3 OD) δ 169.6, 169.5, 138.1, 137.9, 137.8, 135.6, 128.5, 128.4, 128.3, 128.1, 128.0, 127.9, 127.8, , , , 127.5, 127.2, 126.6, 126.5, 124.3, 123.9, 97.3, 81.1, 79.2, 77.1, 77.1, 74.4, 72.8, 69.9, 68.3, 66.7, 65.5, 64.0, 62.8, 53.9, 37.3, HR-ESI-MS m/z: calcd for C 45 H 48 N 6 O 10 +H , found ,6-di-O-benzyl-4,6-di-O-{1-[(1(S)-carboxy-2-p-hydroxyphenylethyl)]-4-methyl-1H-1,2,3-triazole-4 -yl}-α-d-glucopyranoside (24). From compound 22 (131.2 mg, 0.15 mmol), column chromatography (EtOAc/EtOH, 1:1) afforded 24 as a white solid (125.5 mg, 98.7 %). R f = 0.12 (EtOAc/EtOH, 1:1). [α] D = +3.5 (c = 0.6/MeOH). 1 H NMR (400 MHz, DMSO-d6) δ (m, 2H), (m, 10H), (m, 4H), (m, 4H), (m, 2H), 4.89 (dd, 1H, J = 4.8, 11.2 Hz), (m, 2H), (m, 2H), (m, 1H), (m, 3H), (m, 1H), (m, 3H), (m, 6H), (m, 3H). 13 C NMR (100 MHz, DMSO-d6) δ 170.3, 169.9, 156.0, 143.9, 143.8, 138.3, 138.2, 129.8, 128.2, 128.1, 127.9, 127.6, 127.5, 127.4, 126.2, 126.1, 124.1, 123.8, 115.1, 115.0, 97.0, 81.3, 79.0, 77.2, 74.0, 72.2, 69.6, 68.6, 65.6, 63.7, 63.3, 59.7, 54.4, HR-ESI-MS m/z: calcd for C 45 H 48 N 6 O 12 +H , found ,6-di-O-benzyl-3,4-di-O-{1-[(1(S)-carboxy-2-phenylethyl)]-4-methyl-1H-1,2,3-triazole-1,4-diyl}-α- D-glucopyranoside (30). From compound 28 (150.0 mg, 0.17 mmol), column chromatography (EtOAc/EtOH, 1:1) afforded 30 as a yellow solid (133.9 mg, 92.0 %). R f = 0.40 (EtOAc/EtOH, 1:2). [α] D = (c = 0.1/MeOH). 1 H NMR (400 MHz, DMSO-d6) δ 8.00 (s, 1H), 7.89 (s, 1H), (m, 10H), (m, 10H), (m, 2H), (m, 3H), (m, 3H), 4.56 (dd, 1H, J = 5.6, 11.6 Hz), (m, 2H), (m, 3H), (m, 6H), 3.22 (s, 3H), (m, 1H). 13 C NMR (100 MHz, DMSO-d6) δ 170.5, 143.3, 143.1, 138.7, 138.4, 137.4, 137.3, 128.7, 128.6, 128.2, 128.1, 128.1, 127.5, 127.4, 126.4, 123.6, 96.9, 81.0, 78.6, 77.2, 74.4, 74.2, 72.3, 69.6, 68.8, 65.4, 63.2, 63.1, 54.3, 37.7, HR-ESI-MS m/z: calcd for C 45 H 48 N 6 O 10 +Na , found ,6-di-O-benzyl-3,4-di-O-{1-[(1(S)-carboxy-2-p-hydroxyphenylethyl)]-4-methyl-1H-1,2,3-triazole-4 -yl}-α-d-glucopyranoside (31). From compound 29 (165.0 mg, 0.18 mmol), column chromatography (EtOAc/EtOH, 1:2) afforded 31 as a yellow solid (148.0 mg, 92.6 %). R f = 0.40 (EtOAc/EtOH, 1:2). [α] D = -9.1 (c = 0.1/MeOH). 1 H NMR (400 MHz, DMSO-d6) δ 7.97 (s, 1H), 7.85 (s, 1H), (m, 10H), (m, 4H), (m, 4H), 5.24 (brs, 2H), (m, 3H), (m, 3H), (m, 3H), (m, 6H), (m, 7H). 13 C NMR (100 MHz, DMSO-d6) δ 170.9, 155.9, 143.1, 142.9, 138.7, 138.4, 129.5, 128.2, 128.0, 127.7, 127.5, 127.4, 127.3, 123.4, 115.0, 97.0, 81.1, 79.2, 78.8, 77.2, 74.4, 72.3, 69.6, 68.8, 66.7, 65.4, 63.5, 54.3, 37.5, HR-ESI-MS m/z: calcd for C 45 H 48 N 6 O 12 +H , found ,4-di-O-{1-[(1(S)-carboxy-2-p-hydroxyphenylethyl)]-4-methyl-1H-1,2,3-triazole-4-yl}-α-D-glucop yranoside (33). Saponification of compound 32 (103.7 mg, 0.15 mmol) afforded 33 as a white solid (95.6 mg, 99.6 %) without column chromatography. R f = 0.45 (petroleum ether/etoac, 1:4). [α] D = (c = 0.1/MeOH). 1 H NMR (400 MHz, CD 3 OD) δ 8.73 (s, 1H), 8.64 (s, 1H), (m, 4H), (m, 4H), (m, 2H), (m, 5H), 3.56 (t, 1H, J = 12.0 Hz), (m, 1H), (m, 6H), 2.90 (s, 3H), (m, 2H). 13 C NMR (100 MHz, CD 3 OD) δ 187.6, 170.2, 155.6, 155.3, 137.1, 133.2, 132.1, 130.6, 130.4, 130.2, 118.8, 118.7, 97.0, 74.2, 72.4, 72.3, 66.7, 63.5, 56.1, 54.3, 54.2, 51.1, 42.6, 21.2, HR-ESI-MS m/z: calcd for C 31 H 36 N 6 O 12 +H , found Preparation of compound 32. To a biphasic solution of 26 (150.0 mg, 0.30 mmol) and b (166.5 mg, 0.75 mmol) in CH 2 Cl 2 (5 ml) and H 2 O (5 ml), Na ascorbate (298.2 mg, 1.51 mmol) and CuSO 4 5H 2 O (225.8 mg, 0.90 mmol) were added. After stirring for 8 h at rt. (until TLC indicated the disappearance of the starting materials), the mixture was diluted with CH 2 Cl 2, washed with water, dried over MgSO 4, filtered and evaporated to give a crude residue which was purified by column chromatography (petroleum ether/etoac = 2:1 to 1:1) to afford the corresponding triazole (282.8 mg, 81.4%). This product (150.0 mg, 0.16 mmol) was then desilylated according to the general procedure. Further purification by column chromatography (CH 2 Cl 2 /MeOH, 12:1) afforded 32 as a white solid (103.7 mg, 91.2 %). R f = 0.29 (CH 2 Cl 2 /MeOH, 10:1). [α] D = (c = 0.1/MeOH). 1 H NMR (400 MHz, CDCl 3 ) δ 9.14 (brs, 1H), 8.83 (brs, 1H), 7.76 (s, 1H), 7.63 (s, 1H), (m, 8H), 5.68 (dd, 1H, J = 5.0,
5 Hz), 5.47 (dd, 1H, J = 4.2, 12.4 Hz), 5.02 (d, 1H, J = 13.3 Hz), 4.82 (d, 1H, J = 13.7 Hz), 4.76 (d, 1H, J = 3.7 Hz), 4.70 (d, 1H, J = 13.7 Hz), 4.56 (d, 1H, J = 13.8 Hz), 3.84 (s, 3H), 3.83 (s, 3H), (m, 2H), 3.70 (t, 1H, J = 13.7 Hz), 3.58 (dd, 1H, J = 4.6, 15.1 Hz), (m, 2H), 3.35 (s, 3H), (m, 2H), 3.02 (dd, 1H, J = 3.7, 9.2 Hz), 2.79 (t, 1H, J = 9.2 Hz), 2.47 (brs, 1H), 2.26 (s, 1H); 13 C NMR (100 MHz, CDCl 3 ) δ 168.9, 156.5, 144.9, 129.5, 124.8, 124.4, 116.2, 115.9, 96.6, 77.5, 76.8, 72.9, 72.3, 69.9, 64.9, 63.4, 62.0, 61.8, 60.5, 59.8, 55.3, 55.2, 53.5, 38.3, HR-ESI-MS m/z: calcd for C 33 H 40 N 6 O 12 +H , found
Supporting Information
Supporting Information for AgOTf-catalyzed one-pot reactions of 2-alkynylbenzaldoximes with α,β-unsaturated carbonyl compounds Qiuping Ding 1, Dan Wang 1, Puying Luo* 2, Meiling Liu 1, Shouzhi Pu* 3 and
Διαβάστε περισσότεραA facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 A facile and general route to 3-((trifluoromethyl)thio)benzofurans and 3-((trifluoromethyl)thio)benzothiophenes
Διαβάστε περισσότεραDivergent synthesis of various iminocyclitols from D-ribose
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 205 Divergent synthesis of various iminocyclitols from D-ribose Ramu Petakamsetty,
Διαβάστε περισσότεραElectronic Supplementary Information
Electronic Supplementary Information Unprecedented Carbon-Carbon Bond Cleavage in Nucleophilic Aziridine Ring Opening Reaction, Efficient Ring Transformation of Aziridines to Imidazolidin-4-ones Jin-Yuan
Διαβάστε περισσότεραCopper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic acids with the assistance of isocyanide
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Copper-catalyzed formal O-H insertion reaction of α-diazo-1,3-dicarb- onyl compounds to carboxylic
Διαβάστε περισσότεραRoom Temperature Highly Diastereoselective Zn-Mediated. Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled
Supporting Information for: Room Temperature Highly Diastereoselective Zn-Mediated Allylation of Chiral N-tert-Butanesulfinyl Imines: Remarkable Reaction Condition Controlled Stereoselectivity Reversal
Διαβάστε περισσότεραDirect Palladium-Catalyzed Arylations of Aryl Bromides. with 2/9-Substituted Pyrimido[5,4-b]indolizines
Direct Palladium-Catalyzed Arylations of Aryl Bromides with 2/9-Substituted Pyrimido[5,4-b]indolizines Min Jiang, Ting Li, Linghua Meng, Chunhao Yang,* Yuyuan Xie*, and Jian Ding State Key Laboratory of
Διαβάστε περισσότεραSupporting Information
Supporting Information Lewis acid catalyzed ring-opening reactions of methylenecyclopropanes with diphenylphosphine oxide in the presence of sulfur or selenium Min Shi,* Min Jiang and Le-Ping Liu State
Διαβάστε περισσότεραEnantioselective Organocatalytic Michael Addition of Isorhodanines. to α, β-unsaturated Aldehydes
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2016 Enantioselective Organocatalytic Michael Addition of Isorhodanines to α,
Διαβάστε περισσότεραSupplementary information
Electronic Supplementary Material (ESI) for MedChemComm. This journal is The Royal Society of Chemistry 2015 Supplementary information Synthesis of carboxyimidamide-substituted benzo[c][1,2,5]oxadiazoles
Διαβάστε περισσότεραSupporting Information
Supporting Information Copper/Silver Cocatalyzed Oxidative Coupling of Vinylarenes with ICH 2 CF 3 or ICH 2 CHF 2 Leading to β-cf 3 /CHF 2 -Substituted Ketones Niannian Yi, Hao Zhang, Chonghui Xu, Wei
Διαβάστε περισσότεραSite-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran
1 Site-Selective Suzuki-Miyaura Cross-Coupling Reactions of 2,3,4,5-Tetrabromofuran Munawar Hussain, a Rasheed Ahmad Khera, a Nguyen Thai Hung, a Peter Langer* a,b a Institut für Chemie, Universität Rostock,
Διαβάστε περισσότεραSupporting Information
Supporting Information for Lewis acid-catalyzed redox-neutral amination of 2-(3-pyrroline-1-yl)benzaldehydes via intramolecular [1,5]-hydride shift/isomerization reaction Chun-Huan Jiang, Xiantao Lei,
Διαβάστε περισσότεραSupporting Information. Synthesis and biological evaluation of 2,3-Bis(het)aryl-4-azaindoles Derivatives as protein kinases inhibitors
Supporting Information Synthesis and biological evaluation of 2,3-Bis(het)aryl-4-azaindoles Derivatives as protein kinases inhibitors Frédéric Pin, a Frédéric Buron, a Fabienne Saab, a Lionel Colliandre,
Διαβάστε περισσότεραPeptidomimetics as Protein Arginine Deiminase 4 (PAD4) Inhibitors
Peptidomimetics as Protein Arginine Deiminase 4 (PAD4) Inhibitors Andrea Trabocchi a, icolino Pala b, Ilga Krimmelbein c, Gloria Menchi a, Antonio Guarna a, Mario Sechi b, Tobias Dreker c, Andrea Scozzafava
Διαβάστε περισσότεραSupporting Information
Supporting Information An Approach to 3,6-Disubstituted 2,5-Dioxybenzoquinones via Two Sequential Suzuki Couplings. Three-step Synthesis of Leucomelone Xianwen Gan, Wei Jiang, Wei Wang,,,* Lihong Hu,,*
Διαβάστε περισσότεραSupporting Information for
Supporting Information for An atom-economic route to densely functionalized thiophenes via base-catalyzed rearrangement of 5-propargyl-2H-thiopyran-4(3H)-ones Chunlin Tang a, Jian Qin b, Xingqi Li *a a
Διαβάστε περισσότεραNovel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans. Supporting Information
Novel and Selective Palladium-Catalyzed Annulation of 2-Alkynylphenols to Form 2-Substituted 3-Halobenzo[b]furans Liang Yun, Shi Tang, Xu-Dong Zhang, Li-Qiu Mao, Ye-Xiang Xie and Jin-Heng Li* Key Laboratory
Διαβάστε περισσότεραEffect of uridine protecting groups on the diastereoselectivity
Supporting Information for Effect of uridine protecting groups on the diastereoselectivity of uridine-derived aldehyde 5 -alkynylation Raja Ben Othman, Mickaël J. Fer, Laurent Le Corre, Sandrine Calvet-Vitale*
Διαβάστε περισσότεραDirect Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3
Supporting Information Direct Transformation of Ethylarenes into Primary Aromatic Amides with N-Bromosuccinimide and I 2 -aq NH 3 Shohei Shimokawa, Yuhsuke Kawagoe, Katsuhiko Moriyama, Hideo Togo* Graduate
Διαβάστε περισσότεραHiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl
Hiyama Cross-Coupling of Chloro-, Fluoroand Methoxy- pyridyl trimethylsilanes : Room-temperature Novel Access to Functional Bi(het)aryl Philippe Pierrat, Philippe Gros* and Yves Fort Synthèse Organométallique
Διαβάστε περισσότεραSynthesis of novel 1,2,3-triazolyl derivatives of pregnane, androstane and D-homoandrostane. Tandem Click reaction/cu-catalyzed D-homo rearrangement
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting Information Synthesis of novel 1,2,3-triazolyl derivatives of
Διαβάστε περισσότεραSupporting Information. Synthesis and biological evaluation of nojirimycin- and
Supporting Information for Synthesis and biological evaluation of nojirimycin- and pyrrolidine-based trehalase inhibitors Davide Bini 1, Francesca Cardona 2, Matilde Forcella 1, Camilla Parmeggiani 2,3,
Διαβάστε περισσότεραSupporting information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 Supporting information Copper-catalysed intramolecular O-arylation: a simple
Διαβάστε περισσότεραand Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol
FeCl 3 6H 2 O-Catalyzed Disproportionation of Allylic Alcohols and Selective Allylic Reduction of Allylic Alcohols and Their Derivatives with Benzyl Alcohol Jialiang Wang, Wen Huang, Zhengxing Zhang, Xu
Διαβάστε περισσότεραSynthesis and evaluation of novel aza-caged Garcinia xanthones
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Synthesis and evaluation of novel aza-caged Garcinia xanthones Xiaojin Zhang, a,1 Xiang Li, a,1 Haopeng Sun, * b Zhengyu Jiang,
Διαβάστε περισσότεραSupporting Information. Design and Synthesis of 2-Arylbenzimidazoles and. Evaluation of Their Inhibitory Effect against. Chlamydia pneumoniae
Supporting Information Design and Synthesis of 2-Arylbenzimidazoles and Evaluation of Their Inhibitory Effect against Chlamydia pneumoniae Leena Keurulainen,, Olli Salin,, Antti Siiskonen,, Jan Marco Kern,
Διαβάστε περισσότεραSupporting Information. Asymmetric Binary-acid Catalysis with Chiral. Phosphoric Acid and MgF 2 : Catalytic
Supporting Information Asymmetric Binary-acid Catalysis with Chiral Phosphoric Acid and MgF 2 : Catalytic Enantioselective Friedel-Crafts Reactions of β,γ- Unsaturated-α-Ketoesters Jian Lv, Xin Li, Long
Διαβάστε περισσότεραFluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine Reagents. An Efficient Method for 1,3- Oxyfluorination and 1,3-Difluorination
Electronic Supplementary Material (ESI) for Chemical Science. This journal is The Royal Society of Chemistry 2016 Supporting Information Fluorinative Ring-opening of Cyclopropanes by Hypervalent Iodine
Διαβάστε περισσότεραPhosphorus Oxychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions
Supplementary Information for Phosphorus xychloride as an Efficient Coupling Reagent for the Synthesis of Ester, Amide and Peptide under Mild Conditions u Chen,* a,b Xunfu Xu, a Liu Liu, a Guo Tang,* a
Διαβάστε περισσότεραTributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate
upporting Information Tributylphosphine-Catalyzed Cycloaddition of Aziridines with Carbon Disulfide and Isothiocyanate Jing-Yu Wu, Zhi-Bin Luo, Li-Xin Dai and Xue-Long Hou* a tate Key Laboratory of Organometallic
Διαβάστε περισσότεραSupplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%.
Supplementary Figure S1. Single X-ray structure 3a at probability ellipsoids of 20%. S1 Supplementary Figure S2. Single X-ray structure 5a at probability ellipsoids of 20%. S2 H 15 Ph Ac Ac I AcH Ph Ac
Διαβάστε περισσότεραSupporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of. 1,2,3-Triazole Synthesis
Supporting Information for: Intramolecular Hydrogen Bonding-Assisted Cyclocondensation of α-diazoketones with Various Amines: A Strategy for Catalytic Wolff 1,2,3-Triazole Synthesis Zikun Wang, a Xihe
Διαβάστε περισσότεραSupporting Information for
Supporting Information for Palladium-Catalyzed C-H Bond Functionalization of C6-Arylpurines Hai-Ming Guo,* Wei-Hao Rao, Hong-Ying iu, Li-Li Jiang, Ge ng, Jia-Jia Jin, Xi-ing Yang, and Gui-Rong Qu* College
Διαβάστε περισσότεραSupporting Information
Supporting Information 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Convenient and General Zinc-Catalyzed Borylation of Aryl Diazonium Salts and Aryltriazenes under Mild Conditions
Διαβάστε περισσότεραNew Glucuronic Acid Donors for the Modular Synthesis of Heparan Sulfate Oligosaccharides
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 214 Supporting Information New Glucuronic Acid Donors for the Modular Synthesis
Διαβάστε περισσότεραRh(III)-Catalyzed C-H Amidation with N-hydroxycarbamates: A. new Entry to N-Carbamate Protected Arylamines
Rh(III)-Catalyzed C-H Amidation with N-hydroxycarbamates: A new Entry to N-Carbamate Protected Arylamines Bing Zhou,* Juanjuan Du, Yaxi Yang,* Huijin Feng, Yuanchao Li Shanghai Institute of Materia Medica,
Διαβάστε περισσότεραMetal-free Oxidative Coupling of Amines with Sodium Sulfinates: A Mild Access to Sulfonamides
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting information for Metal-free Oxidative Coupling of Amines with Sodium Sulfinates:
Διαβάστε περισσότεραSupporting Information
Supporting Information Montmorillonite KSF-Catalyzed One-pot, Three-component, Aza-Diels- Alder Reactions of Methylenecyclopropanes With Arylaldehydes and Aromatic Amines Li-Xiong Shao and Min Shi* General
Διαβάστε περισσότεραFirst DMAP-mediated direct conversion of Morita Baylis. Hillman alcohols into γ-ketoallylphosphonates: Synthesis of
Supporting Information File 1 for First DMAP-mediated direct conversion of Morita Baylis Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates Marwa Ayadi 1,2, Haitham Elleuch
Διαβάστε περισσότερα9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer catalysts
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2014 9-amino-(9-deoxy)cinchona alkaloids-derived novel chiral phase-transfer
Διαβάστε περισσότεραSupporting Information
Supporting Information Enantiospecific Synthesis of the Cubitane Skeleton Elisabeth Schöttner, M. Wiechoczek, Peter G. Jones, and Thomas Lindel * TU Braunschweig, Institutes of rganic, Inorganic and Analytical
Διαβάστε περισσότεραSupporting Information One-Pot Approach to Chiral Chromenes via Enantioselective Organocatalytic Domino Oxa-Michael-Aldol Reaction
Supporting Information ne-pot Approach to Chiral Chromenes via Enantioselective rganocatalytic Domino xa-michael-aldol Reaction Hao Li, Jian Wang, Timiyin E-Nunu, Liansuo Zu, Wei Jiang, Shaohua Wei, *
Διαβάστε περισσότεραCopper-Catalyzed Oxidative Dehydrogenative N-N Bond. Formation for the Synthesis of N,N -Diarylindazol-3-ones
Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers. This journal is the Partner Organisations 2016 Supporting information Copper-Catalyzed Oxidative Dehydrogenative - Bond Formation
Διαβάστε περισσότεραESI for. A simple and efficient protocol for the palladium-catalyzed. ligand-free Suzuki reaction at room temperature in aqueous DMF.
ESI for A simple and efficient protocol for the palladium-catalyzed ligand-free Suzuki reaction at room temperature in aqueous DMF Chun Liu,* Qijian i, Fanying Bao and Jieshan Qiu State Key Laboratory
Διαβάστε περισσότεραDiastereoselective Access to Trans-2-Substituted Cyclopentylamines
Supporting Information Diastereoselective Access to Trans-2-Substituted Cyclopentylamines Antoine Joosten, Emilie Lambert, Jean-Luc Vasse, Jan Szymoniak jean-luc.vasse@univ-reims.fr jan.szymoniak@univ-reims.fr
Διαβάστε περισσότεραSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 1 A Facile Way to Synthesize 2H-Chromenes: Reconsideration of the Reaction Mechanism between Salicylic Aldehyde and
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for rganic Chemistry Frontiers. This journal is the Partner rganisations 2018 Palladium-catalyzed direct approach to α-cf 3 aryl ketones from arylboronic acids Bo
Διαβάστε περισσότεραAsymmetric Synthesis of New Chiral β-amino Acid Derivatives by Mannich-type Reactions of Chiral N- Sulfinyl Imidates with N-Tosyl Aldimines
Asymmetric Synthesis of New Chiral β-amino Acid Derivatives by Mannich-type Reactions of Chiral N- Sulfinyl Imidates with N-yl Aldimines Filip Colpaert, Sven Mangelinckx, and Norbert De Kimpe Department
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Synthesis of 3-omosubstituted Pyrroles via Palladium- Catalyzed Intermolecular Oxidative Cyclization
Διαβάστε περισσότεραSupporting Information
Supporting Information Metal-catalyzed Stereoselective and Protecting-group-free Synthesis of 1,2-cis-Glycosides Using 4,6-Dimethoxy-1,3,5-triazin-2-yl Glycosides as Glycosyl Donors Tomonari Tanaka,* 1
Διαβάστε περισσότεραVilsmeier Haack reagent-promoted formyloxylation of α-chloro-narylacetamides
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 205 Vilsmeier aack reagent-promoted formyloxylation of α-chloro-arylacetamides by formamide Jiann-Jyh
Διαβάστε περισσότεραAminofluorination of Fluorinated Alkenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Synthesis of ɑ CF 3 and ɑ CF 2 H Amines via Aminofluorination of Fluorinated Alkenes Ling Yang,
Διαβάστε περισσότεραLewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes
Supporting Information for Lewis Acid Catalyzed Propargylation of Arenes with O-Propargyl Trichloroacetimidate: Synthesis of 1,3-Diarylpropynes Changkun Li and Jianbo Wang* Beijing National Laboratory
Διαβάστε περισσότεραSupporting Information
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2018 Supporting Information Silver or Cerium-Promoted Free Radical Cascade Difunctionalization
Διαβάστε περισσότεραSupporting Information
Supporting Information Wiley-VCH 2007 69451 Weinheim, Germany Supporting Information for Catalytic Enantioselective Conjugate Reduction of β,β- Disubstituted α,β-unsaturated sulfones Tomás Llamas, Ramón
Διαβάστε περισσότεραSupplementary Data. Engineering, Nanjing University, Nanjing , P. R. China;
Supplementary Data Synthesis, Chemo-selective Properties of Substituted 9-Aryl-9H-fluorenes from Triarylcarbinols and Enantiomerical Kinetics of Chiral 9-Methoxy-11-(naphthalen-1-yl)-11H-benzo[a]fluorene
Διαβάστε περισσότεραSupporting Information
Supporting Information Wiley-VCH 2014 69451 Weinheim, Germany Copper-Catalyzed Coupling of Oxime Acetates with Sodium Sulfinates: An Efficient Synthesis of Sulfone Derivatives** Xiaodong Tang, Liangbin
Διαβάστε περισσότεραFacile construction of the functionalized 4H-chromene via tandem. benzylation and cyclization. Jinmin Fan and Zhiyong Wang*
Facile construction of the functionalized 4H-chromene via tandem benzylation and cyclization Jinmin Fan and Zhiyong Wang* Hefei National Laboratory for Physical Science at Microscale, Joint- Lab of Green
Διαβάστε περισσότεραCopper-Catalyzed Oxidative Coupling of Acids with Alkanes Involving Dehydrogenation: Facile Access to Allylic Esters and Alkylalkenes
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2014 Supplementary information Copper-Catalyzed xidative Coupling of Acids with Alkanes Involving Dehydrogenation:
Διαβάστε περισσότεραThe N,S-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H. Carbonylation using Langlois Reagent as CO Source. Supporting Information.
Electronic upplementary Material (EI) for rganic & Biomolecular Chemistry. This journal is The Royal ociety of Chemistry 2018 The,-Bidentate Ligand Assisted Pd-Catalyzed C(sp 2 )-H Carbonylation using
Διαβάστε περισσότεραSupporting Information for. Catalytic C H α-trifluoromethylation of α,β-unsaturated Carbonyl Compounds
Supporting Information for Catalytic C H α-trifluoromethylation of α,β-unsaturated Carbonyl Compounds Zhongxue Fang, a Yongquan Ning, a Pengbing Mi, a Peiqiu Liao, a Xihe Bi* a,b a Department of Chemistry,
Διαβάστε περισσότεραSupporting Information
Supporting Information First Total Synthesis of Neoantimycin Hikaru Ogawa, Hideo Iio, and Yoshinosuke Usuki* Division of Molecular MaterialsScience, Graduate School of Science, Osaka City University, 3-3-138
Διαβάστε περισσότεραOxidative Activation of C S Bonds with an Electropositive Nitrogen Promoter Enables Orthogonal Glycosylation of Alkyl over Phenyl Thioglycosides
Supporting Information Oxidative Activation of C S Bonds with an Electropositive Nitrogen Promoter Enables Orthogonal Glycosylation of Alkyl over Phenyl Thioglycosides Annabel Kitowski,, Ester Jiménez-Moreno,
Διαβάστε περισσότεραRegioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone.
Regioselectivity in the Stille coupling reactions of 3,5- dibromo-2-pyrone. Won-Suk Kim, Hyung-Jin Kim and Cheon-Gyu Cho Department of Chemistry, Hanyang University, Seoul 133-791, Korea Experimental Section
Διαβάστε περισσότεραSupporting Information. Consecutive hydrazino-ugi-azide reactions: synthesis of acylhydrazines bearing 1,5- disubstituted tetrazoles
Supporting Information for Consecutive hydrazino-ugi-azide reactions: synthesis of acylhydrazines bearing 1,5- disubstituted tetrazoles Angélica de Fátima S. Barreto*, Veronica Alves dos Santos, and Carlos
Διαβάστε περισσότεραSupporting Information
Supporting Information Ceric Ammonium Nitrate (CAN) catalyzed efficient one-pot three component aza-diels-alder reactions for a facile synthesis of tetrahydropyranoquinoline derivatives Ravinder Goud Puligoundla
Διαβάστε περισσότεραAluminium-mediated Aromatic C F Bond Activation: Regioswitchable Construction of Benzene-fused Triphenylene. Frameworks
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2016 Aluminium-mediated Aromatic C Bond Activation: Regioswitchable Construction of Benzene-fused Triphenylene
Διαβάστε περισσότεραSupporting information
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Supporting information TFA-promoted Direct C H Sulfenylation at the C2 position of non-protected
Διαβάστε περισσότεραElectronic Supplementary Information
Electronic Supplementary Material (ESI) for Polymer hemistry This journal is The Royal Society of hemistry 2011 Phosphoric and Phosphoramidic Acids as Bifunctional atalysts for the Ring-pening Polymerization
Διαβάστε περισσότεραCopper-Catalyzed Direct Acyloxylation of C(sp 2 ) H Bonds. in Aromatic Amides
Supporting Information for Copper-Catalyzed Direct Acyloxylation of C(sp 2 ) H Bonds in Aromatic Amides Feifan Wang, Qiyan Hu, Chao Shu, Zhiyang Lin, Dewen Min, Tianchao Shi and Wu Zhang* Key Laboratory
Διαβάστε περισσότεραSupporting Information. Chemoselective Acylation of 2-Amino-8-quinolinol in the Generation of C2-Amides or C8-Esters
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2017 Supporting Information Chemoselective Acylation of 2-Amino-8-quinolinol in the Generation of
Διαβάστε περισσότεραConstruction of Cyclic Sulfamidates Bearing Two gem-diaryl Stereocenters through a Rhodium-Catalyzed Stepwise Asymmetric Arylation Protocol
Supporting Information for: Construction of Cyclic Sulfamidates Bearing Two gem-diaryl Stereocenters through a Rhodium-Catalyzed Stepwise Asymmetric Arylation Protocol Yu-Fang Zhang, Diao Chen, Wen-Wen
Διαβάστε περισσότεραSupporting Information. Table of Contents. II. Experimental procedures. II. Copies of 1H and 13C NMR spectra for all compounds
Electronic upplementary Material (EI) for rganic & Biomolecular Chemistry. This journal is The Royal ociety of Chemistry 2017 Laboratoire de Méthodologie et ynthèse de Produit aturels. Université du Québec
Διαβάστε περισσότεραNatural Products Research Institute, College of Pharmacy, Seoul National University, 1 Gwanak-ro, Gwanak-gu, Seoul 08826, Republic of Korea
Supporting Information Nicrophorusamides A and B, Antibacterial Chlorinated Cyclic Peptides from a Gut Bacterium of the Carrion Beetle Nicrophorus concolor Yern-Hyerk Shin, Suhyun Bae, Jaehoon Sim,,ǁ Joonseong
Διαβάστε περισσότεραSupporting Information
Supporting Information Structure-Activity and Structure-Property Relationship and Exploratory in vivo Evaluation of the Nanomolar Keap1-Nrf2 Protein-Protein Interaction Inhibitor Zheng-Yu Jiang, a,b Li-Li
Διαβάστε περισσότεραSelective mono reduction of bisphosphine
Griffith Research Online https://research-repository.griffith.edu.au Selective mono reduction of bisphosphine oxides under mild conditions Author etersson, Maria, Loughlin, Wendy, Jenkins, Ian ublished
Διαβάστε περισσότεραSupplementary Information for
Supplementary Information for Organocatalytic Asymmetric Intramolecular [3+2] Cycloaddition: A Straightforward Approach to Access Multiply Substituted Hexahydrochromeno[4,3-b]pyrrolidine Derivatives in
Διαβάστε περισσότεραPalladium-Catalyzed C H Monoalkoxylation of α,β-unsaturated Carbonyl Compounds
Supporting Information Palladium-Catalyzed C H Monoalkoxylation of α,β-unsaturated Carbonyl Compounds Yasunari Monguchi,* Kouki Kunishima, Tomohiro Hattori, Tohru Takahashi, Yuko Shishido, Yoshinari Sawama,
Διαβάστε περισσότεραSynthesis of spiropyrazoline oxindoles by a formal [4+1] annulation reaction between 3-bromooxindoles and in situ-derived 1,2-diaza-1,3- dienes
Electronic Supplementary Material (ESI) for rganic Chemistry Frontiers. This journal is the Partner rganisations 2017 Supporting Information for Synthesis of spiropyrazoline oxindoles by a formal [4+1]
Διαβάστε περισσότεραCrossed Intramolecular Rauhut-Currier-Type Reactions via Dienamine Activation
Crossed Intramolecular Rauhut-Currier-Type Reactions via Dienamine Activation Eugenia Marqués-López, Raquel P. Herrera, Timo Marks, Wiebke C. Jacobs, Daniel Könning, Renata M. de Figueiredo, Mathias Christmann*
Διαβάστε περισσότεραSupporting Materials
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 Carbonylative Coupling of Aryl Tosylates/triflates with Arylboronic Acids under CO Atmosphere
Διαβάστε περισσότεραElectronic Supplementary Information (ESI)
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry Electronic Supplementary Information (ESI) For Iron-Catalysed xidative Amidation of Alcohols with Amines Silvia Gaspa, a Andrea
Διαβάστε περισσότεραSupporting Information
Supporting Information Transition-metal-free Ring Expansion Reactions of Indene-1,3-dione: Synthesis of Functionalized Benzoannulated Seven-Membered Ring Compounds Qiyi Yao, Lingkai Kong, Mengdan Wang,
Διαβάστε περισσότεραSI1. Supporting Information. Synthesis and pharmacological evaluation of conformationally restricted -opioid receptor agonists
Electronic Supplementary Material (ESI) for MedChemComm. This journal is The Royal Society of Chemistry 2016 SI1 Supporting Information Synthesis and pharmacological evaluation of conformationally restricted
Διαβάστε περισσότεραSupporting Information for. Copper-Catalyzed Radical Reaction of N-Tosylhydrazones: Stereoselective Synthesis of (E)-Vinyl Sulfones
Supporting Information for Copper-Catalyzed Radical Reaction of N-Tosylhydrazones: Stereoselective Synthesis of (E)-Vinyl Sulfones Shuai Mao, Ya-Ru Gao, Xue-Qing Zhu, Dong-Dong Guo, Yong-Qiang Wang* Key
Διαβάστε περισσότεραSupporting Information
Supporting Information Selective Synthesis of xygen-containing Heterocycles via Tandem Reactions of 1,2-Allenic Ketones with Ethyl 4-Chloroacetoacetate Qiang Wang, a, b Zhouqing Xu b and Xuesen Fan a *
Διαβάστε περισσότεραFree Radical Initiated Coupling Reaction of Alcohols and. Alkynes: not C-O but C-C Bond Formation. Context. General information 2. Typical procedure 2
Free Radical Initiated Coupling Reaction of Alcohols and Alkynes: not C-O but C-C Bond Formation Zhongquan Liu,* Liang Sun, Jianguo Wang, Jie Han, Yankai Zhao, Bo Zhou Institute of Organic Chemistry, Gannan
Διαβάστε περισσότεραSupporting information
Supporting information Synthesis of Aryl Sulfides: Metal-Free C H Sulfenylation of Electron-Rich Arenes Thomas Hostier, a Vincent Ferey, b Gino Ricci, c Domingo Gomez Pardo a and Janine Cossy*, a a Laboratoire
Διαβάστε περισσότεραSupporting Information for
Supporting Information for A ovel Synthesis of luorinated Pyrazoles via Gold(I)-Catalyzed Tandem Aminofluorination of Alkynes in the Presence of Selectfluor Jianqiang Qian, Yunkui Liu,* Jie Zhu, Bo Jiang,
Διαβάστε περισσότεραKOtBu-Mediated Stereoselective Addition of Quinazolines to. Alkynes under Mild Conditions
KOtBu-Mediated Stereoselective Addition of Quinazolines to Alkynes under Mild Conditions Dan Zhao, Qi Shen, Yu-Ren Zhou, and Jian-Xin Li* State Key lab of Analytical Chemistry for Life Science, School
Διαβάστε περισσότεραCatalyst-free transformation of levulinic acid into pyrrolidinones with formic acid
Catalyst-free transformation of levulinic acid into pyrrolidinones with formic acid Yawen Wei, a Chao Wang,* a Xue Jiang, a Dong Xue, a Zhao-Tie Liu, a and Jianliang Xiao* a,b a Key Laboratory of Applied
Διαβάστε περισσότεραSupporting Information for Synthesis of Fused N-Heterocycles via Tandem C-H Activation
This journal is The Royal Society of Chemistry 212 Supporting Information for Synthesis of Fused -Heterocycles via Tandem C-H Activation Ge Meng, Hong-Ying iu, Gui-Rong Qu, John S. Fossey, Jian-Ping Li,*
Διαβάστε περισσότεραTotal Synthesis of Echinopines A and B
Total Synthesis of Echinopines A and B K. C. Nicolaou,* anfeng Ding, Jean-Alexandre Richard, and David Y.-K. Chen* Contribution from Chemical Synthesis Laboratory@Biopolis, Institute of Chemical and Engineering
Διαβάστε περισσότεραSupporting Information. Preparation of aminoethyl glycosides for glycoconjugation
Supporting Information for Preparation of aminoethyl glycosides for glycoconjugation Robert Šardzík, Gavin T. Noble, Martin J. Weissenborn, Andrew Martin, Simon Webb and Sabine L. Flitsch* Address: Manchester
Διαβάστε περισσότεραSupporting Information
Supporting Information Gold-catalyzed Cycloisomerization of 1,6-Diyne-4-en-3-ols to form Naphthyl Ketone Derivatives. Jian-Jou Lian and Rai-Shung Liu* Department of Chemistry, National Tsing-Hua University,
Διαβάστε περισσότεραSupporting information
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 204 Supporting information Palladium nanoparticles supported on triazine functionalised mesoporous
Διαβάστε περισσότεραSupplementary Figures
Supplementary Figures Supplementary Figure 1. 1 H NMR spectra for 1-(2-iodopropyl)-3-(trifluoromethyl)benzene Supplementary Figure 2. 13 C NMR spectra for 1-(2-iodopropyl)-3-(trifluoromethyl)benzene Supplementary
Διαβάστε περισσότεραSupporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2006
Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 Silver-Catalyzed Asymmetric Synthesis of 2,3-Dihydrobenzofurans: A New Chiral Synthesis of Pterocarpans Leticia Jiménez-González, Sergio
Διαβάστε περισσότεραThe Free Internet Journal for Organic Chemistry
The Free Internet Journal for Organic Chemistry Paper Archive for Organic Chemistry Arkivoc 2018, part iii, S1-S6 Synthesis of dihydropyranones and dihydropyrano[2,3- d][1,3]dioxine-diones by cyclization
Διαβάστε περισσότερα