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1 Supporting Information for Removal of benzylidene acetal and benzyl ether in carbohydrate derivatives using triethylsilane and Pd/C Abhishek Santra, Tamashree Ghosh and Anup Kumar Misra * Address: Bose Institute, Division of Molecular Medicine, P-1/12, C.I.T. Scheme VII-M, Kolkata , India; FAX: Anup Kumar Misra - akmisra69@gmail.com *Corresponding author Analytical data of new compounds, 1 H NMR and 13 C NMR spectra Analytical data of new compounds: acetylated-8, 14, 16, acetylated-18, 22 and acetylated S2 NMR spectra of compounds 2, 4, acetylated-6, acetylated-8, 10, 12, 14, 16, acetylated-18, 22, acetylated-24, 27, S5 S1
2 Analytical data of new compounds 2-(p-Methoxyphenoxy)ethyl 2,3,4,6-tetra--acetyl- -D-mannopyranoside (acetylated-8): 25 Colorless oil; [ ] D + 39 (c 1.0, CHCl 3 ); IR (neat): 2566, 1759, 1377, 1229, 1166, 1053, 916 cm 1 ; 1 H NMR (CDCl 3, 500 MHz): δ (m, 4 H, Ar-H), 5.24 (dd, J = 10.0 Hz, 3.0 Hz, 1 H, H-3), (m, 1 H, H-2), 5.18 (t, J = 10.0 Hz each, 1 H, H-4), 4.83 (d, J = 1.5 Hz, 1 H, H-1), 4.19 (dd, J = 12.0 Hz, 5.0 Hz, 1 H, H-6 a ), (m, 2 H, H-5, H-6 b ), (m, 2 H, CH 2 ), (m, 1 H, CH 2 ), (m, 1 H, CH 2 ), 3.69 (s, 3 H, CH 3 ), 2.09, 2.01, 1.96, 1.92 (4s, 12 H, 4 CCH 3 ); 13 C NMR (CDCl 3, 125 MHz): δ 170.4, 169.8, 169.6, (4 CCH 3 ), (Ar-C), 97.7 (C-1), 69.5 (C-2), 69.0 (C-3), 68.6 (CH 2 ), 67.4 (CH 2 ), 66.9 (C-4), 66.1 (C-5), 62.3 (C-6), 55.6 (CH 3 ), 20.9, 20.7, 20.6 (2 C) (4 CCH 3 ); ESIMS: [M + Na] + ; Anal. calcd for C 23 H (498.17): C, 55.42; H, 6.07; found: C, 55.25; H, p-methoxyphenyl 2,3-di--acetyl- -D-galactopyranoside (14): Colorless oil; [ ] D + 14 (c 1.0, CHCl 3 ); IR (neat): 2988, 2942, 1748, 1433, 1377, 1226, 1085, 1056, 918, 756 cm 1 ; 1 H NMR (CDCl 3, 500 MHz): δ 6.84 (d, J = 9.0 Hz, 2 H, Ar-H), 6.70 (d, J = 9.0 Hz, 2 H, Ar-H), 5.40 (dd, J = 8.0 Hz each, 1 H, H-2), 4.90 (dd, J = 10.5, 3.5 Hz, 1 H, H-3), 4.85 (d, J = 8.0 Hz, 1 H, H-1), 4.11 (br s, 1 H, H-4), (m, 2 H, H-6 ab ), 3.67 (s, 3 H, CH 3 ), (m, 1 H, H-5), 3.44, 2.92 (2 br s, 1 H each, 2 H), 2.03, 1.99 (2s, 6 H, 2 CCH 3 ); 13 C NMR (CDCl 3, 125 MHz): δ 170.3, (2 CCH 3 ), (Ar-C), (C-1), 74.4 (C-5), 73.4 (C-3), 69.3 (C-4), 67.8 (C-2), 62.0 (C-6), 55.5 (CH 3 ), 20.8, 20.7 (2 CCH 3 ); ESIMS: [M + Na] + ; Anal. calcd for C 17 H 22 9 (370.12): C, 55.13; H, 5.99; found: C, 54.97; H, n-propyl 2,3-di--acetyl- -D-galactopyranoside (16): Colorless oil; [ ] D , CHCl 3 ); IR (neat): 2928, 2853, 1744, 1371, 1222, 1045, 914, 761 cm 1 ; 1 H NMR (CDCl 3, 500 MHz): δ 5.17 (dd, J = 8.0 Hz each, 1 H, H-2), 4.83 (dd, J = 10.5, 3.5 Hz, 1 H, H-3), 4.39 (d, J = 7.5 Hz, 1 H, H-1), 4.08 (d, J = 3.0 Hz, 1 H, H-4), (m, 3 H, H-6 ab, CH 2 ), (m, 1 H, H-5), (m, 1 H, CH 2 ), 2.02, 1.97 (2 s, 6 H, 2 CCH 3 ), (m, 2 H, CH 2 ), 0.85 (t, J = 7.5 Hz each, 3 H, CH 3 ); 13 C NMR (CDCl 3, 125 MHz): δ 170.3, (2 CCH 3 ), (C-1), 74.0 (C-5), 73.5 (CH 2 ), 71.6 (C-3), 69.5 (C-2), 68.0 (C-4), 62.0 (C-6), 22.7 (CH 2 ), 20.8, 20.7 (2 CCH 3 ), 10.3 (CH 3 ); ESIMS: [M + Na] + ; Anal. calcd for C 13 H 22 8 (306.13): C, 50.97; H, 7.24; found: C, 50.79; H, S2
3 6-Bromohexyl 2-acetamido-3,4,6-tri--acetyl-2-deoxy- -D-galactopyranoside (acetylated ): Colorless oil; [ ] D + 55 (c 1.0, CHCl 3 ); IR (neat): 2994, 2947, 1756, 1444, 1356, 1233, 1087, 1056, 915, 756 cm 1 ; 1 H NMR (CDCl 3, 500 MHz): δ 5.59 (d, J = 9.5 Hz, 1 H, NH), 5.35 (d, J = 3.0 Hz, 1 H, H-1), 5.15 (dd, J = 11.0, 3.0 Hz, 1 H, H-3), 4.85 (d, J = 4.0 Hz, 1 H, H-4), (m, 1 H, H-5), (m, 3 H, H-2, H-6 ab ), (m, 1 H, CH 2 ), (m, 1 H, CH 2 ), (m, 2 H, CH 2 ), 2.17, 2.04, 2.00, 1.96 (4 s, 12 H, 4 CCH 3 ), (m, 4 H, CH 2 ); 13 C NMR (CDCl 3, 125 MHz): δ 170.8, (2 C), (4 CCH 3 ), 97.6 (C-1), 68.4 (C-3), 68.2 (CH 2 ), 67.3 (C-5), 66.6 (C-4), 61.8 (C-6), 51.2 (C-2), 47.9 (CH 2 ), 29.2 (CH 2 ), 28.8 (CH 2 ), 26.5 (CH 2 ), 25.8 (CH 2 ), 23.2 (NHCCH 3 ), 20.7 (2 C), 20.6 (3 CCH 3 ); ESIMS: [M + Na] + ; Anal. calcd for C 20 H 32 BrN 9 (509.12): C, 47.07; H, 6.32; found: C, 46.90; H, p-methoxyphenyl -(2,3-di--acetyl- -D-glucopyranosyl)-(1 4)-2,3,6-tri--acetyl- -Dglucopyranoside (22): Colorless oil; [ ] D + 43 (c 1.0, CHCl 3 ); IR (neat): 2928, 2856, 1746, , 1372, 1229, 1041, 759, 602 cm 1 ; 1 H NMR (CDCl 3, 500 MHz): δ 6.90 (d, J = 9.0 Hz, 2 H, Ar-H), 6.76 (d, J = 9.0 Hz, 2 H, Ar-H), 5.33 (d, J = 3.5 Hz, 1 H, H-1 B ), 5.27 (t, J = 9.0 Hz each, 1 H, H-2 A ), 5.19 (t, J = 9.0 Hz each, 1 H, H-3 A ), 5.03 (t, J = 8.0 Hz each, 1 H, H-3 B ), 4.97 (t, J = 8.0 Hz, 1 H, H-1 A ), 4.71 (dd, J = 10.5, 3.0 Hz, 1 H, H-2 B ), 4.50 (d, J = 12.0 Hz, 1 H, H-6 aa ), 4.21 (dd, J = 12.0, 5.0 Hz, 1 H, H-6 ba ), 4.05 (t, J = 9.5 Hz each, 1 H, H-4 B ), (m, 3 H, H-4 A, H-5 A, H-5 B ), 3.74 (s, 3 H, CH 3 ), (m, 2 H, H-6 abb ), 2.09, 2.06, 2.02, 2.00 (5 s, 15 H, 5 CCH 3 ); 13 C NMR (CDCl 3, 125 MHz): δ 171.1, 171.8, 170.7, 170.2, (5 CCH 3 ), (Ar-C), 99.5 (C-1 B ), 95.7 (C-1 A ), 75.4 (C-3 B ), 72.8 (C-3 A ), 72.3 (C-4 A ), 72.2 (C-4 B ), 72.0 (C-2 B ), 71.8 (C-2 A ), 70.4 (C-5 B ), 69.2 (C-5 A ), 62.9 (C-6 B ), 61.8 (C-6 A ), 55.5 (CH 3 ), 20.9, 20.8 (2 C), 20.6, 20.5 (5 CCH 3 ); ESIMS: [M + Na] + ; Anal. calcd for C 29 H (658.21): C, 52.89; H, 5.82; found: C, 52.74; H, p-methoxyphenyl -(2,3,4-tri--acetyl- -L-rhamnopyranosyl)-(1 3)-2-acetamido-4,6-di- 25 -acetyl-2-deoxy- -D-glucopyranoside (acetylated-24): Colorless oil; [ ] D + 63 (c 1.0, CHCl 3 ); IR (neat): 2957, 2924, 2592, 1745, 1433, 1376, 1239, 1044, 890 cm 1 ; 1 H NMR (CDCl 3, 500 MHz): δ 6.98 (d, J = 9.0 Hz, 2 H, Ar-H), 6.83 (d, J = 9.0 Hz, 2 H, Ar-H), 5.86 (dd, J = 9.5, 3.5 Hz, 1 H, NH), 5.41 (d, J = 3.5 Hz, 1 H, H-1 A ), (m, 3 H, H-2 B, H-3 B, H-4 B ), 5.04 (t, J = 10.0 Hz each, 1 H, H-4 A ), 4.86 (br s, 1 H, H-1 B ), 4.57 (t, J = 10.5 Hz each, 1 H, H-2 A ), (m, 2 H, H-6 aba ), (m, 3 H, H-3 A, H-5 A, H-5 B ), 3.77 (s, 3 H, CH 3 ), 2.16, 2.11, 2.08, 2.04, 2.03, 1.97 (6 CCH 3 ), 1.14 (d, J = 6.0 Hz, 3 H, CCH 3 ); 13 C NMR (CDCl 3, S3
4 125 MHz): δ (4 C), (2 C) (6 CCH 3 ), (Ar-C), 99.8 (C-1 A ), 97.0 (C-1 B ), 80.3 (C-3 A ), 70.5 (C-5 A ), 70.1 (C-2 B ), 69.9 (C-3 B ), 68.9 (C-4 A ), 68.6 (C-4 B ), 67.6 (C-5 B ), 61.8 (C-6 A ), 55.6 (CH 3 ), 51.9 (C-2 A ), 23.2 (NHCCH 3 ), 21.1, 21.0, 20.8, 20.7, 20.6 (5 CCH 3 ), 17.2 (CCH 3 ); ESIMS: [M + Na] + ; Anal. calcd for C 31 H 41 N 16 (683.24): C, 54.46; H, 6.04; found: C, 54.30; H, S4
5 H H CH3 2 S5
6 H 4 H SE Ac CCl 4 S6
7 Ac C 8 H 17 Ac Acetylated-6 S7
8 Ac Acetylated-8 PMP CCl 4 S8
9 H H CH 3 NPhth 10 S9
10 H H PMP NPhth 12 CCl 4 S10
11 H H PMP Ac 14 CCl 4 S11
12 H H Ac 16 CCl 4 S12
13 Ac C 6 H 12 Br NHAc Acetylated-18 CCl 4 S13
14 H H 22 Ac PMP S14
15 AcHN PMP Ac Acetylated-24 CCl 4 S15
16 H Bz H Bz CH3 27 S16
17 H H Ac PMP 29 S17
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