Divergent synthesis of various iminocyclitols from D-ribose
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1 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, Vipin Kumar Jain, Pankaj Kumar Majhi and Ramesh Ramapanicker* Department of Chemistry and Center for Environmental Science and Engineering Indian Institute of Technology Kanpur Kanpur, India Supplementary Information Contents Page umbers. General experimental procedures and procedure for the synthesis of benzyl derivatives for MR Correlation 2. MR correlation data for benzyl derivatives 3. and 3 C MR spectra for all the compounds 4. PLC Data
2 Procedure for Benzyl Protection: Compounda(0.8 g, 2 mmol, equiv) in DMF (0 ml) was added to a stirred suspension of sodium hydride (0.4 g, 6 mmol, 3 equiv) in DMF (5 ml) at 0 ºC under nitrogen atmosphere and stirring was continued for 20 min. Benzyl bromide (0.7 ml, 6 mmol, 3 equiv) was added to the reaction mixture and stirred at room temperature for 4 h. After complete disappearance of starting material on TLC, the reaction was quenched with water (30 ml). rganic layer was extracted with diethyl ether (2 20 ml), and the combined organic phases were washed with brine ( 20 ml), dried over anhydrous a 2 S 4, filtered, concentrated, and purified by column chromatography. TBDPS a, DMF, BnBr 0 C to rt 4h TBDPS Ph 5 2 Ph 7 8 0a 30a (89%) Compound (30): Column chromatography (petroleum ether/etac, 9:); oily liquid (0.2 g, 0.33 mmol, 89%); [α] 25 D = +2.8 (c 0.8, CCl 3 ); IR ν max (thin film):3068, 56 cm - ; MR (500 Mz, CDCl 3 ): δ (m, 4, Ar-), (m, 6, Ar-), (m,, C 3 ), 4.66 (m, 3, C,C 0 ), 4.56 (d, J = 6.3 z,, C 2 ), 4. (d, J = 3.7 z,, C 0 ), (m,, C 5 ), (m, 2, C 6 ), (m,, C 5 ), (m,, C 4 ), (m,, C ),.50 (s, 3, C 7 ),.3 (s, 3, C 8 ),.08 (s, 9, (C 3 ) 3 C-Si) ppm; 3 C MR (25 Mz, CDCl 3 ): δ 4.0(C-Ar), 35.8(C-Ar), 35.7(C-Ar), 33.7(C-Ar), 29.7(C-Ar), 28.6(C-Ar), 28.5(C-Ar), 28.4(C-Ar), 27.7(C-Ar), 27.0(C- Ar), 5.5(C-9), 82.(C-), 8.(C-0), 66.6(C-3), 66.5(C-2), 65.3(C-5), 62.6(C-6), 59.3(C-), 52.5(C- 4), 27.0 ((C 3 ) 3 C-Si), 26.5(C-8), 24.8(C-7), 9.3(C-Si) ppm RMS (ESI-TF) m/z [M+] + calcd for C Si ; found
3 MM 8a a, DMF, BnBr 0 C to rt 4h Ph Ph MM a (85%) Compound(3a): In a similar manner as described for compound 30a, Column chromatography (petroleum ether/etac, 9:); oily liquid (0.7 g, 0.39mmol, 85%);[α] 25 D = -9.3 (c 0.2, CCl 3 ); IR ν max (thin film): 3028, 495 cm - ; MR (500 Mz, CDCl 3 ): δ (m, 0, Ar-), 4.64 (d,j = 6.7 z,, --C 2 --), 4.6 (d,j= 7.3z,, --C 2 --), 4.56 (d, J =.6 z,, C 0 ), (m, 2, C 6, C 0 ), (m, 2, C 6, C 9 ), (m,, C 2 ), 3.8 (dd,j = 0.7, 2. z,, C 3 ), 3.59 (dd,j =.0, 4.2 z,, C 4 ), 3.30 (s, 3, -C 3 ), 3.26 (d,j = 3.6z,, C 9 ), 2.77 (dd,j =.0, 5.5 z,, C ), (m,, C 5 ), (t, J =.0 z,, C ),.54 (s, 3, C 7 ),.39 (s, 3, C 8 ) ppm; 3 C MR (25 Mz, CDCl 3 ): δ 39.0(C-Ar), 38.(C-Ar), 28.9(C-Ar), 28.4(C- Ar), 28.3(C-Ar), 27.9(C-Ar), 27.7(C-Ar), 27.0(C-Ar), 09.4(C-), 95.9(--C 2 --), 74.9(C-0), 74.5(C-9), 73.4(C-2), 7.7(C-3), 68.7(C-4), 63.6(C-6), 57.(-C 3 ), 55.5(C-5), 50.5(C-), 28.2(C-8), 26.3(C-7) ppm; RMS (ESI-TF) m/z [M+] + calcd for C ; found Ph MM. a, DMF, BnBr 0 C to rt 4h 2. 2, Pd/C,rt, 4 h Me MM b 3b (69%) 7 3
4 Compound(3b):Column chromatography (petroleum ether/etac, :); oily liquid (0. g, 0.32mmol, 69%);[α] 25 D = +2.2 (c 0.8, CCl 3 ); IRν max (thin film): 308, 495 cm - ; MR (500 Mz, CDCl 3 ): δ (m, 4, Ar-), (m,, Ar-), 4.74 (d, J = 6.8 z,, --C 2 --), 4.66 (d, J = 6.8 z,, --C 2 --), 4.57 (d, J = 2.0 z,, C 9 ), 4.5 (d, J = 2.0 z,, C 9 ), 4.35 (dd,j = 6.8, 4.0 z,, C 3 ), 4.24 (dd, J = 7.4, 2.8 z,, C 4 ), (m,, C 2 ), (m, 2, C 6 ), 3.37 (s, 3 C 3 ), 3.09 (dd, J = 3., 6.8 z,, C ), 3.03 (dt, J = 6.8, 2.3 z,, C 5 ), 2.88 (dd, J = 3., 4.6 z,, C ), 2. (bs,, 0 ).42 (s, 3, C 7 ),.38 (s, 3, C 8 )ppm; 3 C MR (25 Mz, CDCl 3 ): δ 38.2(C-Ar), 28.4(C-Ar), 27.8(C-Ar), 27.7(C-Ar), 09.4(C-), 96.(--C 2 --), 73.8(C-9), 73.4(C-2), 73.0(C-3), 70.0(C-4), 69.8(C-6), 55.6(-C 3 ), 54.(C-5), 44.9(C-), 26.0(C-8), 25.0(C-7) ppm; RMS (ESI-TF) m/z [M+] + calcd for C ; found TBDPS 23a a, DMF, BnBr 0 C to rt 4h Ph TBDPS 9 Ph a (85%) 5 4 Compound(32a):Column chromatography (petroleum ether/etac, 9:); oily liquid (0.5 g, 0.23mmol 85%); [α] 25 D = (c 0.2, CCl 3 ); IR ν max (thin film): 3060, 536 cm - ; MR (500 Mz, CDCl 3 ): δ (m, 4, Ar-), (m, 6, Ar-), (m, 3, C 8, C 3 ), 4.3 (d, J = 2.8 z, 2, C 2 ), (m, 2, C 9 ), 3.90 (dd, J = 5.5, 9.5 z,, C 5 ), 3.79 (d, J = 4.9 z,, C 9 ), (m, 3C, C 6 ), (m,, C 4 ), (m,, C 4 ),.55 (s, 3, C 0 ),.35 (s, 3, C ),.05 (s, 9, (C 3 ) 3 C-Si) ppm; 3 C MR (25 Mz, CDCl 3 ): δ 4.9(C-Ar), 38.6(C-Ar), 35.7(C-Ar), 35.6(C-Ar), 34.9(C-Ar), 33.7(C-Ar), 29.7(C-Ar), 29.6(C-Ar), 28.7(C-Ar), 28.6(C- Ar), 28.5(C-Ar), 28.4(C-Ar), 28.2(C-Ar), 28.0(C-Ar), 27.7(C-Ar), 27.6(C-Ar), 27.5(C-Ar), 26.5(C-Ar), 08.0(C-2), 73.0(C-8), 73.00(C-6), 72.8(C-9), 7.6(C-7), 63.3(C-2), 58.0(C-3), 55.9(C-), 4
5 55.2(C-5), 27.5(C-4), 27.5(C-0), 26.9(C 3 ) 3 C-Si, 24.8(C-), 9.3(C-Si) ppm; RMS (ESI-TF) m/z [M+] + calcd for C Si ; found TBDPS 23b a, DMF, BnBr 0 C to rt 4h Ph TBDPS 9 Ph b (89%) Compound(32b):Column chromatography (petroleum ether/etac, 9:); oily liquid (0.2 g, 0.3mmol 89%); [α] 25 D = -9. (c 0.8, CCl 3 ); IR ν max (thin film):3059, 589 cm - ; MR (400 Mz, CDCl 3 ): δ (m, 4Ar-), (m, 6, Ar-), (m,, C 2 ), (m, 2, C 8, C 3 ), (m,, C 8 ), (m, 2, C 6 ), (m, 2, C 9 ), (m,, C 7 ), (m,, C 7 ), (m,, C ) (m,, C 5 ), (m,, C 4 ), (m,, C 4 ),.50 (s, 3, C ),.33 (s, 3, C 0 ), 0.99 (s, 9, (C 3 ) 3 C-Si)) ppm; 3 C MR (00 Mz, CDCl 3 ): δ 4.9(C-Ar), 38.3(C-Ar), 35.69(C-Ar), 35.6(C-Ar), 33.7(C-Ar), 33.6(C-Ar), 29.5(C-Ar), 28.3(C-Ar), 28.0(C-Ar), 27.8(C-Ar), 27.6(C-Ar), 27.5(C-Ar), 26.3(C-Ar), 08.2(C- 2), 73.2(C-8), 73.(C-3), 72.9(C-2), 72.4(C-6), 64.0(C-7), 62.6(C-9), 58.6(C-), 53.0(C-5), 28.4(C-4), 28.(C-0), 26.8(C 3 ) 3 C-Si, 25.6(C-), 9.2(C-Si) ppm RMS (ESI-TF) m/z[(m+)-(cl)] + calcd for C Si ; found Ph MM a, DMF, BnBr 0 C to rt 4h Ph MM a 0 33a (86%) 5
6 Compound(33a):Column chromatography (petether/ethyl acetate 8:2); oily liquid (0.3 g, 0.67 mmol 86%); [α] 25 D = +8.6 (c 0.22, CCl 3 ); IR ν max (thin film): 2947, 436 cm - ; MR (500 Mz, CDCl 3 ): δ (m, 0, Ar-), (m, 4, --C 2 --, C 4, C 9 ), (m, 2, C 9, C 3 ), 4.00 (d, J = 9.7 z,, C 5 ), 3.78 (d, J = 4.3 z,, C 8 ), 3.60 (d, J = 4.3 z,, C 8 ), 3.56 (dd, J = 9.7, 7. z,, C 7 ), 3.47 (dd, J = 9.7, 5.7 z,, C 7 ), (m,, C ), 3.29 (s, 3, -C 3 ), 3.20 (dd, J = 4.3, 0.0 z,, C 6 ), 2.65 (d, J = 4.9 z,, C 6 ), (m, 2, C 2 ),.54 (s, 3, C ),.38 (s, 3, C 0 ) ppm; 3 C MR (25 Mz, CDCl 3 ): δ 40.0 (C-Ar), 38.3 (C-Ar), 28.8 (C-Ar), 28.4 (C-Ar), 28.3 (C-Ar), 27.9 (C-Ar), 27.6 (C-Ar), 27.0 (C-Ar), 07.7 (C-2), 94.9 (-- C 2 --), 79.2 (C-9), 73.4 (C-4), 73. (C-3), 72.7 (C-5), 69.8 (C-8), 56.0 (C-7), 55.6 (-C 3 ), 50.6 (C-), 50. (C-6), 36.2 (C-2), 29.7 (C-0), 25.9 (C-) ppm; RMS (ESI-TF) m/z [M+] + calcd for C ; found Ph MM a, DMF, BnBr 0 C to rt 4h Ph MM b 0 33b (86%) Compound(33b):Column chromatography (petether/ethyl acetate 8:2); oily liquid (0.25 g, 0.56 mmol, 87%); [α] 25 D = +3.3 (c.6, CCl 3 ); IR ν max (thin film): 2947, 436 cm - ; MR (400 Mz, CDCl 3 ): δ (m, 0, Ar-), 4.62 (d, J = 8.6 z,, --C 2 --), (m, 5, --C 2 --, C 4, C 9, C 3 ), (m, 2, C 5, C 8 ), 3.79 (dd, J = 2.6, 8.6 z,, C 7 ), 3.74 (d, J = 7.7 z,, C 8 ), 3.47 (dd, J = 2.0, 6.3 z,, C 7 ), 3.28 (s, 3, -C 3 ), (m, 2, C 6, C ), 2.70 (dd, J = 8.9, 6.9 z,, C 6 ), (m,, C 2 ), (m,, C 2 ),.47 (s, 3, C ),.36 (s, 3, C 0 ) ppm; 3 C MR (00 Mz, CDCl 3 ): δ 40.3 (C-Ar), 38.5 (C-Ar), 28.5 (C-Ar), 28.4 (C-Ar), 28.3 (C-Ar), 27.6 (C-Ar), 27.0 (C-Ar), 07.4 (C-2), 96.3 (--C 2 --), 78.3 (C-9), 75.5 (C-4),
7 (C-3), 73.3 (C-5), 70.4 (C-8), 59.4 (C-7), 58.2 (-C 3 ), 55.4 (C-), 48.3 (C-6), 32.4 (C-2), 26.8 (C-0), 24.3 (C-) ppm; RMS (ESI-TF) m/z [M+] + calcd for C ; found
8 MR Correlation data for benzyl derivatives Compound 30 TBDPS Bn Bn MR (500 Mz, CDCl 3 ) TBDPS Bn Bn 3 C MR (25 Mz, CDCl 3 ) 8
9 TBDPS Bn Bn - CSY (500 Mz) 9
10 TBDPS 5 4 Bn 2 3 Bn ne spectrum (irradiation of -4) 0
11 Compound 3a Bn Bn MM MR (500 Mz, CDCl 3 ) Bn Bn MM 3 C MR (25 Mz, CDCl 3 )
12 Bn Bn MM - CSY (500 Mz) 2
13 5.4% 5 MM 4 Bn 6 2 Bn 3 ne spectrum (irradiation of -2) 3
14 Compound 3b Bn MM MR (500 Mz, CDCl 3 ) spectrum of Bn MM 3 C MR (25 Mz, CDCl 3 ) 4
15 Bn MM - CSY (500 Mz) 5
16 5 MM 4 Bn Bn 2 3.2% ne spectrum (irradiation of -4) 6
17 Compound32a TBDPS Bn Bn MR (500 Mz, CDCl 3 ) TBDPS Bn Bn 3 C MR (25 Mz, CDCl 3 ) 7
18 TBDPS Bn Bn CSY (500 Mz) 8
19 TBDPS 5 6 Bn Bn 2 4 ne spectrum (irradiation of -2) 9
20 Compound 32b TBDPS Bn Bn MR (500 Mz, CDCl 3 ) TBDPS Bn Bn 3 C MR (25 Mz, CDCl 3 ) 20
21 TBDPS Bn Bn - CSY (500 Mz) 2
22 7.9% TBDPS 5 6 Bn Bn % ne spectrum (irradiation of -2) 22
23 Compound 33a Bn Bn MM MR (500 Mz, CDCl 3 ) Bn Bn MM 3 C MR (25 Mz, CDCl 3 ) 23
24 Bn Bn MM - CSY (500 Mz) 24
25 4.8% 3 2 Bn 7 MM 4 5 Bn ne spectrum (irradiation of -2) 25
26 Compound 33b Bn Bn MM MR (500 Mz, CDCl 3 ) Bn Bn MM 3 C MR (25 Mz, CDCl 3 ) 26
27 Bn Bn MM - CSY (500 Mz) 27
28 8.8% 8.2% 3 2 Bn 7 MM 4 5 Bn ne spectrum (irradiation of -2) 28
29 Compound 6 TBDPS MR (500 Mz, CDCl 3 ) TBDPS 3 C MR (25 Mz, CDCl 3 ) 29
30 Compound 7 TBDPS Ms MR (500 Mz, CDCl 3 ) TBDPS Ms 3 C MR (25 Mz, CDCl 3 ) 30
31 Compound 8 TBDPS Ms MR (500 Mz, CDCl 3 ) TBDPS Ms 3 C MR (25 Mz, CDCl 3 ) 3
32 Compound 9 MR (500 Mz, CDCl 3 ) TBDPS Ms 3 C MR (25 Mz, CDCl 3 ) 32
33 Compound0a TBDPS Ms Cbz Cbz MR (500 Mz, CDCl 3 ) TBDPS Ms Cbz Cbz 3 C MR (25 Mz, CDCl 3 ) 33
34 Compound0b TBDPS Ms Cbz Cbz MR (500 Mz, CDCl 3 ) TBDPS Ms Cbz Cbz 3 C MR (25 Mz, CDCl 3 ) 34
35 Compound a TBDPS MR (500 Mz, CDCl 3 ) TBDPS C MR (25 Mz, CDCl 3 ) 35
36 Compound b TBDPS MR (500 Mz, CDCl 3 ) TBDPS C MR (25 Mz, CDCl 3 ) 36
37 Compounda 7 5 Cl MR (500 Mz, D 2 ) spectrum of 7 5 Cl C MR (25 Mz, D 2 ) spectrum of compound a 37
38 Compoundb Cl MR (400 Mz, D 2 ) Cl C MR (00 Mz, D 2 ) 38
39 Compound2 TBDPS MM MR (500 Mz, CDCl 3 ) TBDPS MM 3 C MR (25 Mz, CDCl 3 ) 39
40 Compound 3 MM MR (500 Mz, CDCl 3 ) MM 3 C MR (25 Mz, CDCl 3 40
41 Compound 4 Ms MM MR (500 Mz, CDCl 3 ) Ms MM 3 C MR (25 Mz, CDCl 3 ) 4
42 Compound 5 MM Ms MR (500 Mz, CDCl 3 ) MM Ms 3 C MR (25 Mz, CDCl 3 ) 42
43 Compound6 MM Ms MR (500 Mz, CDCl 3 ) MM Ms 3 C MR (25 Mz, CDCl 3 ) 43
44 Compound7a Ms Cbz Cbz MM MR (500 Mz, CDCl 3 ) Ms Cbz Cbz MM 3 C MR (25 Mz, CDCl 3 ) 44
45 Compound7b Cbz Cbz Ms MM MR (500 Mz, CDCl 3 ) Cbz Cbz Ms MM 3 C MR (25 Mz, CDCl 3 ) 45
46 Compound8a MM MR (500 Mz, CDCl 3 ) MM C MR (25 Mz, CDCl 3 ) 46
47 Compound8b MM MR (500 Mz, CDCl 3 ) MM C MR (25 Mz, CDCl 3 ) 47
48 Compound2a 6 Cl MR (500 Mz, D 2 ) 6 Cl C MR (25 Mz, D 2 ) 48
49 Compound 2b 6 Cl MR (500 Mz, D 2 ) 6 Cl C MR (00 Mz, D 2 ) 49
50 Compound 9 TBDPS Et MR (500 Mz, CDCl 3 ) TBDPS Et 3 C MR (25 Mz, CDCl 3 ) 50
51 Compound 20 TBDPS Ms C 2 Et MR (500 Mz, CDCl 3 ) TBDPS Ms C 2 Et 3 C MR (25 Mz, CDCl 3 ) 5
52 Compound2 TBDPS Ms C MR (500 Mz, CDCl 3 ) TBDPS Ms C 3 C MR (25 Mz, CDCl 3 ) 52
53 Compound2a TBDPS Ms Cbz Cbz MR (500 Mz, CDCl 3 ) TBDPS Ms Cbz Cbz 3 C MR (25 Mz, CDCl 3 ) spectrum of compound 22a 53
54 Compound 22b TBDPS Ms Cbz Cbz MR (500 Mz, CDCl 3 ) TBDPS Ms Cbz Cbz 3 C MR (25 Mz, CDCl 3 ) 54
55 Compound 23a TBDPS MR (500 Mz, CDCl 3 ) TBDPS C MR (25 Mz, CDCl 3 ) 55
56 Compound 23b TBDPS MR (500 Mz, CDCl 3 ) TBDPS C MR (25 Mz, CDCl 3 ) 56
57 Compound 3a Cl MR (500 Mz, CD 3 D) Cl C MR (25 Mz, CD 3 D) 57
58 Compound 3b Cl MR (500 Mz, D 2 ) spectrum of Cl C MR (25 Mz, D 2 ) 58
59 Compound24 TBDPS MM Et MR (500 Mz, CDCl 3 ) TBDPS MM Et 3 C MR (25 Mz, CDCl 3 ) 59
60 Compound25 MM Et MR (500 Mz, CDCl 3 ) MM Et 3 C MR (25 Mz, CDCl 3 ) 60
61 Compound26 Ms MM Et MR (500 Mz, CDCl 3 ) Ms MM Et 3 C MR (25 Mz, CDCl 3 ) 6
62 Compound27 Ms MM MR (500 Mz, CDCl 3 ) Ms MM 3 C MR (25 Mz, CDCl 3 ) 62
63 Compound28a Ms MM Cbz Cbz MR (500 Mz, CDCl 3 ) Ms MM Cbz Cbz 3 C MR (25 Mz, CDCl 3 ) 63
64 Compound28b Ms MM Cbz Cbz MR (500 Mz, CDCl 3 ) Ms MM Cbz Cbz 3 C MR (25 Mz, CDCl 3 ) 64
65 Compound29a MM MR (500 Mz, CDCl 3 ) MM C MR (25 Mz, CDCl 3 ) 65
66 Compound29b MM MR (500 Mz, CDCl 3 ) MM C MR (25 Mz, CDCl 3 ) 66
67 Compound4a MR (400 Mz, D 2 ) spectrum of C MR (00 Mz, D 2 ) spectrum of compound4a 67
68 Compound4b MR (400 Mz, D 2 ) C MR (00 Mz, D 2 ) 68
69 PLC DATA PLC data of compound 0 (racemic) 69
70 PLC data of compound 0a 70
71 PLC data of compound 0b 7
72 PLC data of compound 7 (racemic) 72
73 PLC data of compound 7a 73
74 PLC data of compound 7b 74
75 PLC data of compound 22 (racemic) 75
76 PLC data of compound 22a 76
77 PLC data of compound 22b 77
78 PLC data of compound 28 (racemic) 78
79 PLC data of compound 28a 79
80 PLC data of compound 28b 80
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