Electronic Supporting Information (ESI) Diversion of a thioglycoligase for the synthesis of 1-O-acyl arabinofuranoses
|
|
|
- Αφροδίσια Λούλης
- 5 χρόνια πριν
- Προβολές:
Transcript
1 Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2018 Electronic Supporting Information (ESI) Diversion of a thioglycoligase for the synthesis of 1--acyl arabinofuranoses Q. Pavic, S. Tranchimand, L. Lemiègre and L. Legentil * * laurent.legentil@ensc-rennes.fr Table of content General Experimental details Experimental procedures Kinetics of hydrolysis at different ph of 2 followed by 1 H NMR Reaction monitoring of acylation Stability of acyl-α-l-arabinofuranoses 18 and 19 with enzyme CtAraf51 E173A p S2 p S2 p S6 ps7 ps8 1 H and 13 C NMR spectrum of isolated acyl arabinofuranoses 2, and 30 p S9 1 H NMR spectrum of (R,S)-Ibuprofen-α-L-arabinofuranose ps34 S1
2 General Experimental Details All reagents were purchased from commercial sources and were used without further purification unless noted. 2 -benzimidazolyl-1-thio-α-l-arabinofuranoside 1 was synthesized according to literature procedure. 1 Unless otherwise stated, all reactions were monitored by TLC on Silica Gel 60 F 254. TLC spots were detected under 254 nm UV-light or by staining with cerium ammonium molybdate solution. Column chromatography was performed on Silica Gel (50 µm). Melting points were measured on a Stuart melting point apparatus SMP10. ptical rotations were measured at 20 C on a Perkin- Elmer 341 polarimeter. NMR spectra were recorded at 400 MHz for 1 H and 100 MHz for 13 C. Chemical shifts are given in δ units (ppm) and referenced to DMS-d 6. Coupling constants J were calculated in Hertz (Hz). Proton and carbon NMR peaks were unambiguously assigned by J-Mod (J-Modulated spin echo), CSY (double quantum filtered with gradient pulse for selection), HSQC (gradient echo-anti echo selection and shape pulse) and HMBC (echo-anti echo gradient selection, magnitude mode) correlation experiments. High Resolution Masses were recorded in positive mode using direct Electrospray ionization on a Waters Q-Tof 2 spectrometer. Experimental procedures Expression and purification of CtAraf51 E173A Starting from a glycerol stock, Escherichia coli BL21 DE3 cells expressing CtAraf51 E173A 2 were cultured in 10 ml LB, supplemented with kanamycin (50 µg/ml), at 300 rpm, 37 C, overnight. 1 ml of the resulting saturated culture was subsequently used to prepare 1 L of autoinduction media ZYP-5052 containing 400 µg/ml of kanamycin. Cells were incubated for 72h at 250 rpm, 25 C. After centrifugation, 30 min at 4 C, pellet was resuspended in 100 ml of 50 mm phosphate buffer ph 7. Recombinant proteins were extracted from cell by french press and purified by 20 min heat denaturation step at 70 C, centrifugation 30 min at 4 C followed by purification on Ni affinity column. Enzymatic synthesis of glycosyl esters: General procedure: A mixture of 4 equivalent of carboxylic acid acceptor in phosphate buffer (20 ml, 50 mm, ph = 6) was prepared and ph was adjusted to 6 with NaH 2N. The mutant enzyme Araf51 E173A ( 5 mg, eq) and 2 -benzimidazolyl-1-thio-α-l-arabinofuranoside 1 ( 100 mg, 0.35 mmol, 1 eq) were added. The mixture was stirred at RT for 16 hours. After freeze-drying, the mixture was purified by column chromatography on silica gel (dichloromethane/methanol 99:1 90:10) to yield the corresponding 1- -acyl arabinofuranose. Synthesis of acyl arabinofuranoses 2, and 30: 1-(4 -methoxybenzoyl)-α-l-arabinofuranose (2): Product 2 was synthetized according to the general procedure using 2 -benzimidazolyl-1-thio-α-l-arabinofuranoside 1 (100 mg, 0.35 mmol) and 4- methoxybenzoic acid (216 mg, 1.42 mmol). Column chromatography gave 2 (77 mg, 78%) as a white solid. mp 125 C. [α] D = -15 (c 0.73 in MeH). δh (400 MHz; DMS-d 6 ) 3.47 (dt, 1 H, J 5,5 = 11.8 Hz, J 5,8 = J 5,4 = 5.8 Hz, H-5 ), 3.57 (ddd, 1 H, J 5,5 = 11.8 Hz, J 5,8 = 5.5 Hz, J 5,4 = 3.9 Hz, H-5), 3.81 (m, 1 H, H-3), 3.84 (s, 3 H, H-14), 3.98 (dt, 1 H, J 4,3 = J 4-5 = 5.8 Hz, J 4,5 = 3.9 Hz, H-4), 4.10 (ddd, 1 H, J 2,6 = 4.8 Hz, J 2,3 = S2
3 3.2 Hz, J 2,1 = 1.4 Hz, H-2), 4.88 (t, 1 H J 8,5 = 5.6 Hz, H-8), 5.37 (d, 1 H, J 7,3 = 4.7 Hz, H-7), 5.56 (d, 1 H, J 6,2 = 5.0 Hz H-6), 6.05 (d, 1 H, J 1,2 = 1.1 Hz, H-1), 7.06 (d, 2 H, J = 8.9 Hz, H-12), 7.94 (m, 2 H, J = 8.9 Hz, H-11). δc (100 MHz, DMS) 55.6 (C-14), 61.4 (C-5), 76.8 (C-3), 81.2 (C-2), 86.7 (C-4), (C- 1), (C-12), (C-10), (C-11), (C-13), (C-9). HRMS: m/z = [M + Na] + (expected for C 13 H 16 7 Na + : m/z = ). 1--benzoyl-α-L-arabinofuranose (17): Product 17 was synthetized according to the general procedure using 2 -benzimidazolyl-1-thio-α-l-arabinofuranoside 1 (100 mg, 0.35 mmol) and benzoic acid (173 mg, 1.42 mmol). Column chromatography gave 17 (51 mg, 57%) as a white solid. mp 119 C. [α] D = -16 (c 0.76 in MeH). δh (400 MHz; DMS-d 6 ) 3.48 (m, 1 H, H-5 ), 3.57 (ddd, 1 H, J 5,5 = 11.7 Hz, J 5,8 = 5.4 Hz, J 5,4 = 3.9 Hz, H-5), 3.83 (m, 1 H, H-3), 4.00 (ddd, 1 H, J 4,3 = J 4,5 = 5.7 Hz, J 4,5 = 3.9 Hz, H-4), 4.12 (ddd, 1 H, J 2,6 = 4.8 Hz, J 2,3 = 3.3 Hz, J 2,1 = 1.3 Hz, H-2), 4.90 (t, 1 H, J H 8,5 = 5.4 Hz, H-8), 5.39 (d, 1 H, J H 7,3 = 4.6 Hz, H-7), 5.60 (d, 1 H, J H 6,2 = 4.8 Hz, H-6), 6.09 (d, 1 H, J 1,2 = 1.3 Hz, H-1), 7.55 (m, 2 H, H-12), 7.68 (m, 1 H, H-13), 7.99 (m, 2 H, H-11). δc (100 MHz, DMS) 61.4 (C-5), 76.7 (C-3), 81.2 (C-2), 87.1 (C-4), (C-1), (C-12), (C-11), (C-10), (C-13), (C-9). HRMS: m/z = [M + Na] + (expected for C 12 H 14 6 Na + : m/z = ). 1--(4 -bromobenzoyl)-α-l-arabinofuranose (18): Product 18 was synthetized according to the general procedure using 2 -benzimidazolyl-1-thio-α-l-arabinofuranoside 1 (100 mg, 0.35 mmol) and 4- bromobenzoic acid (281 mg, 1.42 mmol). Column chromatography gave 18 (55 mg, 47%) as a colourless oil. [α] D = -17 (c 0.85 in MeH). δh (400 MHz; DMS-d 6 ) 3.47 (dt, 1 H, J 5,5 = 11.1 Hz, J 5,4 = 4.99 Hz H- 5 ), 3.57 (dt, 1 H, J 5,5 = 11.1 Hz, J 5,4 = 3.6 Hz, H-5), 3.83 (m, 1 H, H-3), 4.00 (m, 1 H, H-4), 4.12 (m, 1 H, H-2), 4.91 (bs, 1 H, H-8), 5.39 (bs, 1 H, H-7), 5.60 (bs, 1 H, H-6), 6.08 (d, 1 H, J 1,2 = 1.2 Hz, H-1), 7.77 (d, 2 H, J 11,12 = 8.6 Hz, H-11), 7.90 (d, 2H, J 12,11 = 8.6 Hz, H-12). δc (100 MHz, DMS) 61.4 (C-5), 76.7 (C-3), 81.1 (C-2), 87.2 (C-4), (C-1), (C-13), (C-10), (C-12), (C-11), (C- 9). HRMS: m/z = [M + Na] + (expected for C 12 H 13 Br 6 Na + : m/z = ). 1-(4 -trifluoromethylbenzoyl)-α-l-arabinofuranose (19): Product 19 was synthetized according to the general procedure using 2 -benzimidazolyl-1-thio-α-l-arabinofuranoside 1 (100 mg, 0.35 mmol) and 4- trifluoromethylbenzoic acid (270 mg, 1.42 mmol). Column chromatography gave 19 (64 mg, 57%) as a white solid. mp degradation above 110 C. [α] D = -3 (c 0.58 in MeH). δh (400 MHz; DMS-d 6 ) 3.48 (ddd, 1 H, J 5,5 = 11.8 Hz, J 5,8 = J 5,4 = 5.5 Hz, H-5 ), 3.57 (ddd, 1 H, J 5,5 = 11.8 Hz, J 5,8 = 5.5 Hz, J 5,4 = 4.1 Hz, H-5), 3.85 (m, 1 H, H-3), 4.03 (m, 1 H, H-4), 4.15 (ddd, 1 H, J 2,6 = 4.8 Hz, J 2,3 = 3.0 Hz, J 2,1 = 1.2 Hz, H-2), 4.92 (t, 1 H J 8,5 = 5.6 Hz, H-8), 5.41 (d, 1 H, J 7,3 = 4.8 Hz, H-7), 5.63 (d, 1 H, J 6,2 = 4.8 Hz H-6), 6.11 (d, 1 H, J 1,2 = 1.2 Hz, H-1), 7.94 (d, 2 H, J = 8.1 Hz, H-12), 8.18 (d, 2 H, J = 8.1 Hz, H-11). δc (100 MHz, DMS) 61.3 (C-5), 76.7 (C-3), 81.1 (C-2), 87.4 (C-4), (C-1), (q, J C-F = Hz, C-14), (q, J C-F = 3.8 Hz, C12), (C-11), (q, J C-F = 32.0 Hz, C-13), (d, J C-F = 1.8 Hz, C-10), (C-9).HRMS: m/z = [M + Na] + (expected for C 13 H 16 7 Na + : m/z = ). 1-(4 -nitrobenzoyl)-α-l-arabinofuranose (20): Product 20 was synthetized according to the general procedure using 2 -benzimidazolyl-1-thio-α-l-arabinofuranoside 1 (100 mg, 0.35 mmol) and 4- nitrobenzoic acid (234 mg, 1.42 mmol). Column chromatography gave 6 (NMR conversion 18%, in mixture with 4-nitrobenzoic acid). δh (400 MHz; DMS-d 6 ) 3.48 (dd, 1 H, J 5,5 = 11.8 Hz, J 5,4 = 5.6 Hz, H- 5 ); 3.58 (dd, 1 H, J 5,5 = 11.8 Hz, J 5,4 = 4.1 Hz, H-5), 3.85 (dd, 1 H, J 3,4 = 5.3 Hz, J 3,2 = 3.0 Hz, H-3), 4.04 (ddd, 1 H, J 4,3 = J 4,5 = 5.6 Hz, J 4,5 = 4.1 Hz, H-4), 4.16 (dd, 1 H, J 2,3 = 3.0 Hz, J 2,1 = 1.3 Hz, H-2), 4.93 (bs, 1 H, H-8), 5.43 (bs, 1 H, H-7), 5.65 (bs, 1 H, H-6), 6.12 (d, 1 H, J 1,2 = 1.1 Hz, H-1), 8.21 (d, 2H, J 12,11 = 9.0 Hz, H-11), 8.38 (d, 2H, J 12,11 = 9.0 Hz, H-12). δc (100 MHz, DMS) 61.3 (C-5), 76.6 (C-3), 81.1 (C-2), 87.5 (C-4), (C-1), (C-12), (C-11), (C-10), (C-13), (C-9). HRMS: m/z = [M + Na] + (expected for C 12 H 13 N 8 Na + : m/z = ). S3
4 1-(4 -hydroxybenzoyl)-α-l-arabinofuranose (21): Product 21 was synthetized according to the general procedure using 2 -benzimidazolyl-1-thio-α-l-arabinofuranoside 1 (100 mg, 0.35 mmol) and 4- hydroxybenzoic acid (196 mg, 1.42 mmol). Column chromatography gave 21 (74 mg, 78%) as a white solid. mp 120 C. [α] D = -73 (c 1.19 in MeH). δh (400 MHz; DMS-d 6 ) (m, 2 H, H-5), 3.80 (dt, 1 H, J 3,4 = J 3,7 = 4.8 Hz, J 3,2 = 3.3 Hz H-3), 3.96 (dt, 1 H, J 4,3 = J 4,5 = 5.8 Hz, J 4,5 = 3.8 Hz, H-4), 4.08 (m, 1 H, H-2), 4.90 (t, 1 H J 8,5 = 5.6 Hz, H-8), 5.38 (d, 1 H, J 7,3 = 4.8 Hz, H-7), 5.57 (d, 1 H, J 6,2 = 5.0 Hz H-6), 6.03 (d, 1 H, J 1,2 = 1.3 Hz, H-1), 6.86 (d, 2 H, J 12,11 = 8.7 Hz, H-12), 7.83 (d, 2 H, J 11,12 = 8.7 Hz, H-11). δc (100 MHz, DMS) 61.4 (C-5), 76.8 (C-3), 81.3 (C-2), 86.8 (C-4), (C-1), (C-12), (C-10), (C-11), (C-13), (C-9). HRMS: m/z = [M + Na] + (expected for C 12 H 14 7 Na + : m/z = ). 1--phenylacetoyl-α-L-arabinofuranose (22): Product 22 was synthetized according to the general procedure using 2 -benzimidazolyl-1-thio-α-l-arabinofuranoside 1 (100 mg, 0.35 mmol) and phenylacetic acid (193 mg, 1.42 mmol). Column chromatography gave 22 (63 mg, 66%) as a colourless oil. [α] D = -18 (c 0.63 in MeH). δh (400 MHz; DMS-d 6 ) 3.42 (dd, 1 H, J 5,5 = 12.0 Hz, J 5,4 = 5.8 Hz,H- 5 ), 3.54 (dd, 1 H, J 5,5 = 12.1 Hz, J 5,4 = 3.4 Hz, H-5), 3.69 (s, 2 H, H-10), 3.75 (dd, 1 H, J 3,4 = 6.0 Hz, J 3,2 = 3.6 Hz, H-3), 3.88 (ddd, 1 H, J 4,3 = J 4,5 = 5.9 Hz, J 4,5 = 3.7 Hz, H-4), 3.96 (dd, 1 H, J 2,3 = 3.6 Hz, J 2,1 = 1.6 Hz, H-2), 4.86 (br s, 1 H, H-8), 5.33 (br s, 1 H, H-7), 5.53 (br s, 1 H, H-6), 5.84 (d, 1 H, J 1,2 = 1.6 Hz, H-1), (m, 5 H, H-Ar). δc (100 MHz, DMS) 40.4 (C-10), 61.2 (C-5), 76.6 (C-3), 81.3 (C-2), 86.5 (C-4), (C-1), (C-14), (C-13), (C-12), (C-11), (C-9). HRMS: m/z = [M + Na] + (expected for C 13 H 16 6 Na + : m/z = ). 1-hexanoyl-α-L-arabinofuranose (23): Product 23 was synthetized according to the general procedure using 2 -benzimidazolyl-1-thio-α-l-arabinofuranoside 1 (100 mg, 0.35 mmol) and hexanoic acid (163 mg, 1.42 mmol). Column chromatography gave 23 (67 mg, 77%) as a viscous liquid. [α] D = -75 (c 0.55 in MeH). δh (400 MHz; DMS-d 6 ) 0.87 (t, 3 H, J 14,13 = 6.9 Hz, H-14), (m, 4 H, H-12, H-13), 1.52 (m, 2 H, H-11), 2.29 (t, 2 H, J 10,11 = 7.4 Hz, H-10), 3.42 (ddd, 1 H, J 5,5 = 11.8 Hz, J 5,4 = 5.8 Hz, J 5,8 H = 5.6 Hz, H-5 ), 3.53 (ddd, 1 H, J 5,5 = 11.8 Hz, J 5,8 H = 5.6 Hz, J 5,4 = 3.7 Hz, H-5), 3.73 (ddd, 1 H, J 3,7 H = 4.8 Hz, J 1,2 = 1.3 Hz, J 3,2 = 3.6 Hz, H-3), 3.85 (dt, 1 H, J 4,3 = 5.8 Hz, J 4,5 = 3.7 Hz, H-4), 3.92 (ddd, 1 H, J 2,6 H = 5.2 Hz, J 2,3 = 3.6 Hz, J 2,1 = 1.6 Hz H-2), 4.84 (t, 1 H J 8 H,5 = 5.6 Hz, H-8), 5.28 (d, 1 H, J 7 H,3 = 4.8 Hz H-7), 5.49 (d, 1 H, J 6 H,2 = 5.2 Hz H-6), 5.82 (d, 1 H, J 1,2 = 1.6 Hz, H-1). δc (100 MHz, DMS) 14.3 (C- 14), (C-12,13), 24.4 (C-11), 34.1 (C-10), 61.7 (C-5), 77.1 (C-3), 81.8 (C-2), 86.8 (C-4), (C- 1), (C-9). HRMS: m/z = [M + Na] + (expected for C 11 H 20 6 Na + : m/z = ). 1-(2,2 -dimethylpropanoyl)-α-l-arabinofuranose (24): Product 24 was synthetized according to the general procedure using 2 -benzimidazolyl-1-thio-α-l-arabinofuranoside (100 mg, 0.35 mmol) and pivaloic acid (143 mg, 1.42 mmol). Column chromatography gave 24 (18 mg, 25%) as colourless oil. [α] D = -78 (c 0.86 in MeH). δh (400 MHz; DMS-d 6 ) 1.13 (s, 9 H, H-11), 3.51 (m, 2 H, H-5), 3.73 (m, 1 H, H-3), 3.88 (dt, 1 H, J 4,3 = J 4,5 = 5.8 Hz, J 4,5 = 3.8 Hz, H-4), 3.46 (m, 1 H, H-2), 4.87 (t, 1 H J 8,5 = 5.6 Hz, H- 8), 5.29 (d, 1 H, J 7,3 = 4.6 Hz, H-7), 5.49 (d, 1 H, J 6,2 = 4.9 Hz H-6), 5.79 (d, 1 H, J 1,2 = 1.6 Hz, H-1). δc (100 MHz, DMS) 26.7 (C-11), 38.4 (C-10), 61.4 (C-5), 76.9 (C-3), 81.3 (C-2), 86.7 (C-4), (C-1), (C-9). HRMS: m/z = [M + Na] + (expected for C 10 H 18 6 Na + : m/z = ). (S)-Ibuprofen-α-L-arabinofuranose (25): Product 25 was synthetized according to the general procedure using 2 -benzimidazolyl-1-thio-α-l-arabinofuranoside 1 (100 mg, 0.35 mmol) and (S)- Ibuprofen (292 mg, 1.42 mmol). Column chromatography gave 25 (99 mg, 83%) as colourless oil. [α] D = -6 (c 0.56 in MeH). δh (400 MHz; DMS-d 6 ) 0.85 (d, 6 H, J 18,17 = 6.7 Hz, H-18), 1.37 (d, 3 H, J 11,10 = 7.2 Hz, H-11), 1.80 (dh, 1 H, J 17,16 = 7.2 Hz, J = 6.7 Hz, H-17), 2.41 (d, 2 H, J 16,17 = 7.2 Hz, H-16), 3.39 (d, 1 H, J 5,5 = 11.9 Hz, H-5 ), 3.48 (m, 1 H, H-5), (m, 3 H, H-3, H-4, H-10), 3.93 (m, 1 H, H-2), 4.81 (bs, 1 H, H-8), 4.93 (bs, 1 H, H-6), 5.26 (bs, 1 H, H-7), 5.82 (d, 1 H, J 1,2 = 1.5 Hz, H-1), 7.10 (d, 2 H, S4
5 J 14,13 = 8.1 Hz, H-14), 7.20 (d, 2 H, J 13,14 = 8.1 Hz, H-13). δc (100 MHz, DMS) 18.4 (C-11), 22.2 (C-18), 29.6 (C-17), (C-10), (C-16), 61.0 (C-5), 76.6 (C-3), 81.3 (C-2), 86.4 (C-4), (C-1), (C-13,14), (C-12,15), (C-9). HRMS: m/z = [M + Na] + (expected for C 18 H 26 6 Na + : m/z = ). 1-(6 -hydroxyhexanoyl)-α-l-arabinofuranose (26): Product 26 was synthetized according to the general procedure using 2 -benzimidazolyl-1-thio-α-l-arabinofuranoside 1 (100 mg, 0.35 mmol) and 6- hydroxyhexanoic acid (188 mg, 1.42 mmol). Column chromatography gave 26 (49 mg, 53%) as a colourless oil. [α] D = -73 (c 1.35 in MeH). δh (400 MHz; DMS-d 6 ) 1.29 (m, 2H, H-12), 1.40 (m, 2H, H- 13), 1.52 (p, 2H, J 11,10 = J 11,12 = 7.4 Hz, H-11), 2.29 (t, 2H, J 10,11 = 7.4 Hz, H-10), 3.36 (m, 3H, H-5, H-14), 3.53 (ddd, 1 H, J 5,5 = 11.6 Hz, J 5,8 = 5.3 Hz, J 5,4 = 3.6 Hz, H-5), 3.73 (dt, 1 H, J 3,4 = J 3,7 = 5.3 Hz, J 3,2 = 3.5 Hz H-3), 3.85 (dt, 1 H, J 4,3 = J 4,5 = 5.8 Hz, J 4,5 = 3.7 Hz, H-4), 3.92 (ddd, 1 H, J 2,6 = 5.2 Hz, J 2,3 = 3.5 Hz, J 2,1 = 1.6 Hz, H-2), 4.69 (t, 1H, J 15,14 = 5.2 Hz, H-15), 4.87 (t, 1 H J 8,5 = 5.6 Hz, H-8), 5.31 (d, 1 H, J 7,3 = 4.9 Hz, H-7), 5.52 (d, 1 H, J 6,2 = 5.2 Hz H-6), 5.82 (d, 1 H, J 1,2 = 1.6 Hz, H-1). δc (100 MHz, DMS) 24.2, 25.0 (C-11, C-12), 32.2, 33.8 (C-10, C-13),60.6 (C-14), 61.3 (C-5), 76.7 (C-3), 81.3 (C-2), 86.4 (C-4), (C- 1), (C-9). HRMS: m/z = [M + Na] + (expected for C 11 H 20 7 Na + : m/z = ). N-Boc-phenylalanine-α-L-arabinofuranose (30): Product 30 was synthetized according to the general procedure using 2 -benzimidazolyl-1-thio-α-l-arabinofuranoside 1 (100 mg, 0.35 mmol) and N-Bocphenylalanine 16 (376 mg, 1.42 mmol). Column chromatography gave 30 (53 mg, 38%) as white solid. mp C. [α] D = +4 (c 1.11 in MeH). δh (400 MHz; DMS-d 6 ) 1.32 (s, 9 H, H-19), 2.85 (dd, 1 H,, J 11,11 = 13.6 Hz, J 11,10 = 10.1 Hz, H-11 ), 3.02 (dd, 1 H,, J 11,11 = 13.6 Hz, J 11,10 = 4.9 Hz, H-11), 3.43 (dd, 1 H, J 5,5 = 11.9 Hz, J 5,4 = 5.8 Hz, H-5 ), 3.54 (dd, 1 H, J 5,5 = 12.0 Hz, J 5,4 = 3.6 Hz, H-5), 3.77 (dd, 1 H, J 3,4 = 5.8 Hz, J 3,2 = 3.5 Hz, H-3), 3.84 (dt, 1 H, J 4,3 = 5.8 Hz, J 4,5 = 3.6 Hz, H-4), 3.99 (dd, 1 H, J 2,3 = 3.5 Hz, J 2,1 = 1.5 Hz, H-2), 4.17 (ddd, 1 H, J 10,11 = 10.0 Hz, J 10,NH = 8.13 Hz, J 10,11 = 4.6 Hz, H-10), 5.84 (d, 1 H, J 1,2 = 1.4 Hz, H-1), (m, 6 H, H-Ar, NH). δc (100 MHz, DMS) 28.2 (C-19), 36.2 (C-11), 55.2 (C-10), 61.0 (C-5), 76.7 (C-3), 78.4 (C-18), 81.3 (C-2), 86.4 (C-4), (C-1), (C-15), (C-Ar), (C-Ar), (C-12), (C-17), (C-9). HRMS: m/z = [M + Na] + (expected for C 19 H 27 N 8 Na + : m/z = ). References 1. R. Euzen, V. Ferrières and D. Plusquellec, J. rg. Chem., 2005, 70, Edward J. Taylor, Nicola L. Smith, Johan P. Turkenburg, S. D'Souza, Harry J. Gilbert and Gideon J. Davies, Biochem. J., 2006, 395, S5
6 Kinetics of hydrolysis at different ph of 2 followed by 1 H NMR S6
7 Reaction monitoring of acylation - with acceptor 4-nitrobenzoic acid n (µmol) Time (hour) 1-(4'-nitrobenzoyl)-α-L-arabinofuranose L-Arabinose 2'-benzimidazolyl-1-thio-α-L-arabinofuranose - with acceptor 2-hydroxybenzoic acid n (µmol) Time (hour) (2'-hydroxybenzoyl)-α-L-arabinofuranose L-arabinose 2'-benzimidazolyl-1-thio-α-L-arabinofuranose S7
8 Stability of acyl-α-l-arabinofuranoses 18 and 19 with enzyme CtAraf51 E173A % Hydrolysis Time (hour) (4'-trifluoromethanebenzoate)-α-L-arabinofuranose (19) 1-(4'-bromobenzoyl)-α-L-arabinofuranose (18) S8
9 1 H and 13 C NMR spectrum of isolated acyl arabinofuranoses 2, and 30 S9
10 H H 2 H S10
11 H H H 2 S11
12 H H H 17 S12
13 H H H 17 S13
14 H Br H H 18 S14
15 H Br H H 18 S15
16 H CF 3 H H 19 S16
17 H CF 3 H H 19 S17
18 H N 2 H 20 H S18
19 H N 2 H 20 H S19
20 H H H H 21 S20
21 H H H H 21 S21
22 H H 22 H S22
23 H H H 22 S23
24 H H H 23 S24
25 H H H 23 S25
26 H H H 24 S26
27 H H H 24 S27
28 H H H 25 S28
29 H H H 25 S29
30 H H H 26 H S30
31 H H H H 26 S31
32 H NH H H 30 S32
33 H NH H H 30 S33
34 1 H NMR spectrum of (R,S)-Ibuprofen-α-L-arabinofuranose S34
Copper-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
A 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
Supporting 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,
Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst- and solvent-free thermal multicomponent domino reaction
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 SUPPRTIG IFRMATI Eco-friendly synthesis of diverse and valuable 2-pyridones by catalyst-
Highly enantioselective cascade synthesis of spiropyrazolones. Supporting Information. NMR spectra and HPLC traces
Highly enantioselective cascade synthesis of spiropyrazolones Alex Zea a, Andrea-Nekane R. Alba a, Andrea Mazzanti b, Albert Moyano a and Ramon Rios a,c * Supporting Information NMR spectra and HPLC traces
Supporting Information. Experimental section
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Experimental section General. Proton nuclear magnetic resonance ( 1
Copper-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
Electronic 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
Supporting 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
Supporting Information. Experimental section
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2014 Supporting Information Experimental section General. Anhydrous solvents were transferred by
Supporting 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, *
Supporting 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
Direct 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
Supporting 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
Divergent 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,
Fluorinative 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
Supporting information
Electronic upplementary Material (EI) for New Journal of Chemistry. This journal is The Royal ociety of Chemistry and the Centre National de la Recherche cientifique 7 upporting information Lipase catalyzed,-addition
Supporting 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
Aminofluorination 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,
Supporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process
Supporting Information for Iron-catalyzed decarboxylative alkenylation of cycloalkanes with arylvinylic carboxylic acids via a radical process Jincan Zhao 1, Hong Fang 1, Jianlin Han* 1,2 and Yi Pan* 1
Metal-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:
Supporting 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
Regioselectivity 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
Supporting 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
Site-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,
Supporting Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2017 Modular Synthesis of Propargylamine Modified Cyclodextrins by a Gold(III)-catalyzed Three Component
Electronic 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
Supporting 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
The 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
Hiyama 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
Vilsmeier 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
Supplementary 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
Enantioselective 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,
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
ESI 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
Supplementary 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
Room 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
Iodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via double C(sp 2 )-H thiolation
Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Iodine-catalyzed synthesis of sulfur-bridged enaminones and chromones via
and 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
Supplementary!Information!
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015! Synthesis)and)characterisation)of)an)open1cage) fullerene)encapsulating)hydrogen)fluoride! Supplementary!Information!
Lewis 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
Tributylphosphine-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
Supporting Information. A catalyst-free multicomponent domino sequence for the. diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3-
Supporting Information for A catalyst-free multicomponent domino sequence for the diastereoselective synthesis of (E)-3-[2-arylcarbonyl-3- (arylamino)allyl]chromen-4-ones Pitchaimani Prasanna 1, Pethaiah
Supporting 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
Supporting 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
Supporting 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,*
First 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
Efficient and Simple Zinc mediated Synthesis of 3 Amidoindoles
Electronic Supplementary Material (ESI) for rganic and Biomolecular Chemistry SUPPRTIG IFRMATI Efficient and Simple Zinc mediated Synthesis of 3 Amidoindoles Anahit Pews-Davtyan and Matthias Beller* Leibniz-Institut
Copper-mediated radical cross-coupling reaction of 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123) with phenols or thiophenols. Support Information
Copper-mediated radical cross-coupling reaction of 2,2-dichloro-1,1,1-trifluoroethane (HCFC-123) with phenols or thiophenols Dr. Xiao un Tang and Prof. Qing un Chen* Key Laboratory of Organofluorine Chemistry,
SUPPORTING INFORMATION
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2016 SUPPORTIG IFORMATIO Visible light-mediated decarboxylative amination of indoline-2- carboxylic
Direct 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](/thumbs/87/95187440.jpg "Direct 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
Electronic Supporting Information. Synthesis and Reactivity of 18 F-Labeled α,α-difluoro-α-aryloxyacetic Acids
Electronic Supporting Information Synthesis and Reactivity of 18 F-Labeled α,α-difluoro-α-aryloxyacetic Acids Tanatorn Khotavivattana,, Samuel Calderwood,, Stefan Verhoog, Lukas Pfeifer, Sean Preshlock,
9-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
Supporting 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
Free 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
Supplement: Intramolecular N to N acyl migration in conformationally mobile 1 -acyl-1- systems promoted by debenzylation conditions (HCOONH 4
Cent. Eur. J. Chem. 9(5) 2011 S164-S175 DI: 10.2478/s11532-011-0082-y Central European Journal of Chemistry Supplement: Intramolecular to acyl migration in conformationally mobile 1 -acyl-1- benzyl-3,4
Supporting 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
Synthesis of Imines from Amines in Aliphatic Alcohols on Pd/ZrO 2 Catalyst at Ambient Conditions
This journal is The Royal Society of Chemistry 213 Synthesis of Imines from Amines in Aliphatic Alcohols on Pd/ZrO 2 Catalyst at Ambient Conditions Wenjing Cui, a Bao Zhaorigetu,* a Meilin Jia, a and Wulan
Kishore Natte, Jianbin Chen, Helfried Neumann, Matthias Beller, and Xiao-Feng Wu*
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 204 Kishore Natte, Jianbin Chen, Helfried Neumann, Matthias Beller, and Xiao-Feng
multicomponent synthesis of 5-amino-4-
Supporting Informartion for Molecular iodine-catalyzed one-pot multicomponent synthesis of 5-amino-4- (arylselanyl)-1h-pyrazoles Camila S. Pires 1, Daniela H. de Oliveira 1, Maria R. B. Pontel 1, Jean
Electronic 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
Supporting 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,
Supporting Information
Supporting Information Wiley-VC 007 9 Weinheim, Germany ew ear Infrared Dyes and Fluorophores Based on Diketopyrrolopyrroles Dipl.-Chem. Georg M. Fischer, Dipl.-Chem. Andreas P. Ehlers, Prof. Dr. Andreas
Supplementary Material
Supplementary Material Control experiments S2 Characterization data for the products S2-S7 References S8 MR spectra for the products S9-S28 S1 Control experiments 2a (99.5 mg, 0.5 mmol), I 2 (50.8 mg,
Synthesis 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
SUPPORTING INFORMATION
SUPPRTING INFRMATIN Per(-guanidino--deoxy)cyclodextrins: Synthesis, characterisation and binding behaviour toward selected small molecules and DNA. Nikolaos Mourtzis, a Kyriaki Eliadou, a Chrysie Aggelidou,
Zuxiao Zhang, Xiaojun Tang and William R. Dolbier, Jr.* Department of Chemistry, University of Florida, Gainesville, FL
Photoredox-Catalyzed Intramolecular Difluoromethylation of -Benzylacrylamides Coupled with a Dearomatizing Spirocyclization: Access to CF2H Containing 2- Azaspiro[4.5]deca-6,9-diene-3,8-diones. Zuxiao
Ligand-free Cu(II)-mediated aerobic oxidations of aldehyde. hydrazones leading to N,N -diacylhydrazines and 1,3,4-oxadiazoles
Electronic Supplementary Material (ESI) for rganic & Biomolecular Chemistry. This journal is The Royal Society of Chemistry 2017 Ligand-free Cu(II)-mediated aerobic oxidations of aldehyde hydrazones leading
Facile 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
Electronic Supplementary Information
Electronic Supplementary Information NbCl 3 -catalyzed [2+2+2] intermolecular cycloaddition of alkynes and alkenes to 1,3-cyclohexadiene derivatives Yasushi Obora,* Keisuke Takeshita and Yasutaka Ishii*
Supporting 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
Ferric(III) Chloride Catalyzed Halogenation Reaction of Alcohols and Carboxylic Acids using - Dichlorodiphenylmethane
Supporting Information Ferric(III) Chloride Catalyzed Halogenation Reaction of Alcohols and Carboxylic Acids using - Dichlorodiphenylmethane Chang-Hee Lee,, Soo-Min Lee,, Byul-Hana Min, Dong-Su Kim, Chul-Ho
Phosphorus 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
Supporting 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
Supporting 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
The 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
Mandelamide-Zinc Catalyzed Alkyne Addition to Heteroaromatic Aldehydes
1 Mandelamide-Zinc Catalyzed Alkyne Addition to Heteroaromatic Aldehydes Gonzalo Blay, Isabel Fernández, Alícia Marco-Aleixandre, and José R. Pedro Departament de Química Orgànica, Facultat de Química,
Supporting 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,
Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes
![Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes](/thumbs/61/45469742.jpg "Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes")
Supporting Information for Copper-promoted hydration and annulation of 2-fluorophenylacetylene derivatives: from alkynes to benzo[b]furans and benzo[b]thiophenes Yibiao Li* 1, Liang Cheng 1, Xiaohang Liu
Supporting Information for Fe-Catalyzed Reductive Coupling of Unactivated Alkenes with. β-nitroalkenes. Contents. 1. General Information S2
Supporting Information for Fe-Catalyzed Reductive Coupling of Unactivated Alkenes with β-nitroalkenes Jing Zheng, Dahai Wang, and Sunliang Cui* College of Pharmaceutical Sciences, Zhejiang University,
Novel 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. Supporting Information](/thumbs/64/50937700.jpg "Novel 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
Rh(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,
Copper-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
Protease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent
Supplementary information for the paper Protease-catalysed Direct Asymmetric Mannich Reaction in Organic Solvent Yang Xue, Ling-Po Li, Yan-Hong He * & Zhi Guan * School of Chemistry and Chemical Engineering,
Aqueous MW eco-friendly protocol for amino group protection.
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 215 Aqueous MW eco-friendly protocol for amino group protection. M. ardi, a. errera Cano, b P. Costanzo,
Supporting 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
Supplementary 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
Synthesis 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,
Supporting Information
S1 Supporting Information Synthesis of 2-Arylated Hydroxytyrosol Derivatives via Suzuki-Myaura Cross-Coupling Roberta Bernini, a Sandro Cacchi, b* Giancarlo Fabrizi, b* Eleonora Filisti b a Dipartimento
A straightforward metal-free synthesis of 2-substituted thiazolines in air
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2015 Supporting Information for A straightforward metal-free synthesis of 2-substituted thiazolines
Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/ bromides in water using oxone-kx(x= Cl or Br)
Electronic Supplementary Material (ESI) for Green Chemistry. This journal is The Royal Society of Chemistry 2014 Oxyhalogenation of thiols and disulfides into sulfonyl chlorides/ bromides in water using
Supplementary Information
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 215 Supplementary Information Zinc monoglycerolate as a catalyst for the conversion of 1,3- and
Supporting Information
Supporting Information Lewis Acid Mediated [2,3]-Sigmatropic Rearrangement of Allylic α-amino Amides. Jan Blid, Peter Brandt, Peter Somfai*, Department of Chemistry, rganic Chemistry, Royal Institute of
Supporting Information To: Synthesis of a xylo-puromycin Analogue
Supporting Information To: Synthesis of a xylo-puromycin Analogue Benoît Y. Michel, Kollappillil S. Krishnakumar and Peter Strazewski* Laboratoire de Synthèse de Biomolécules, Institut de Chimie et Biochimie
gem-dichloroalkenes for the Construction of 3-Arylchromones
Electronic Supplementary Material (ESI) for ChemComm. This journal is The Royal Society of Chemistry 2015 Pd(OAc)2/S=PPh3 Accelerated Activation of gem-dichloroalkenes for the Construction of 3-Arylchromones
Supporting 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,
Supporting Information. Copyright Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, 2007
Supporting Information Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2007 Copyright Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, 2006 Supporting Information for High-Throughput Substrate
Rhodium-Catalyzed Oxidative Decarbonylative Heck-type Coupling of Aromatic Aldehydes with Terminal Alkenes
Electronic Supplementary Material (ESI) for RSC Advances. This journal is The Royal Society of Chemistry 2015 Electronic Supplementary Information Rhodium-Catalyzed Oxidative Decarbonylative Heck-type
SUPPORTING INFORMATION. Transition Metal-Free Arylations of In-Situ Generated Sulfenates with Diaryliodonium Salts
S1 SUPPORTING INFORMATION Transition Metal-Free Arylations of In-Situ Generated Sulfenates with Diaryliodonium Salts Hao Yu, Zhen Li, and Carsten Bolm* Institute of Organic Chemistry, RWTH Aachen University
Supporting Information
Electronic upplementary Material (EI) for Green Chemistry. This journal is The Royal ociety of Chemistry 204 upporting Information ynthesis of sulfonamides via I 2 -mediated reaction of sodium sulfinates