C. Mukherjee and A. K. Misra
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1
(KBr): 1747, 1594, 1381, 1225, 1045 cm21; H NMR (200 MHz, CDCl3): d 7.97
(bs, 1H), 7.82–7.73 (m, 3H), 7.56–7.45 (m, 3H), 5.19 (t, J ¼ 9.1 Hz, 1H, H-2),
4.99 (t, J ¼ 9.6 Hz each, 1H, H-3), 4.96 (t, J ¼ 9.5 Hz each, 1H, H-4), 4.73
(d, J ¼ 9.9 Hz, 1H, H-1), 4.21–4.10 (m, 2H, H-6a,b), 3.73–3.65 (m, 1H, H-5),
2.10, 2.02, 2.0, 1.97 (4 s, 12H, 4 COCH3); 13C NMR (50 MHz, CDCl3): d 170.4,
170.1, 169.3, 169.1, 133.8, 133.3, 130.8, 129.0, 128.7, 128.1 (2C), 127.0 (2C),
126.9, 85.9, 76.3, 74.3, 70.4, 68.5, 62.3, 21.0, 20.9, 20.8 (2C); ESI-MS: m/z
513 [M þ Na]þ; Anal. Calcd. for C24H26O9S (490): C, 58.77; H, 5.34; found C,
58.54; H, 5.58.
Naphthyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-galactopyranoside (entry
11, Table 1): White solid; m.p. 114–1168C; [a]D þ4.8 (c 1.2, CHCl3); IR
1
(KBr): 1743, 1592, 1375, 1224, 1043 cm21; H NMR (200 MHz, CDCl3): d 7.99
(bs, 1 H), 7.82–7.74 (m, 3H), 7.57–7.44 (m, 3H), 5.36 (d, J ¼ 2.8 Hz, 1H,
H-4), 5.20 (t, J ¼ 9.8 Hz each, 1H, H-2), 5.02 (dd, J ¼ 9.6 and 3.2 Hz, 1H,
H-3), 4.75 (d, J ¼ 9.7 Hz, 1H, H-1), 4.19–4.06 (m, 2 H, H-6a,b), 3.92–3.89
(m, 1H, H-5), 2.11, 2.03, 2.0, 1.96 (4 s, 12H, 4 COCH3); 13C NMR (50 MHz,
CDCl3): d 170.7, 170.5, 170.4, 169.8, 133.8, 133.1, 132.3, 130.1, 129.9, 128.8,
128.1, 128.0, 127.0 (2C), 86.9, 74.9, 72.4, 67.7, 67.6, 62.1, 21.2, 21.0, 20.9
(2C); ESI-MS: m/z 513 [M þ Na]þ; Anal. Calcd. for C24H26O9S (490): C,
58.77; H, 5.34; found C, 58.57; H, 5.55.
4-Nitrophenyl 2,3,4,6-tetra-O-acetyl-1-thio-b-D-glucopyranoside (entry
12, Table 1): Yellow solid; m.p. 180–1828C; [a]D 232.7 (c 1.2, CHCl3); IR
(KBr): 2923, 2368, 1753, 1344, 1220, 1042, 770 cm21 1H NMR (200 MHz,
;
CDCl3):
d
8.16 (d, J ¼ 8.9 Hz, 2H), 7.59 (d, J ¼ 8.8 Hz, 2H), 5.28
(t, J ¼ 9.2 Hz, 1 H, H-3), 5.08 (t, J ¼ 9.7 Hz, 1H, H-2), 5.04 (t, J ¼ 9.6 Hz
each, 1H, H-4), 4.89 (d, J ¼ 10.0 Hz, 1H, H-1), 4.25–4.21 (m, 2H, H-6a,b),
3.85–3.80 (m, 1H, H-5), 2.10, 2.08, 2.04, 2.0 (4 s, 12H, 4 COCH3); 13C NMR
(50 MHz, CDCl3): d 170.2, 169.9, 169.2, 169.0, 147.6, 141.6, 131.7 (2C), 124.1
(2 C), 84.6, 76.6, 74.0, 70.0, 68.3, 62.2, 21.0, 20.9, 20.8 (2C); ESI-MS: m/z 508
[M þ Na]þ; Anal. Calcd. for C20H23NO11S (485): C, 49.48; H, 4.78; found C,
49.25; H, 5.02.
4,6-Di-O-acetyl-2,3-dideoxy-3-thiophenyl-D-gluconolactone (entry 1,
Table 2): Yellow oil; [a]D þ30 (c 1.2, CHCl3); IR (Neat): 2929, 1747, 1669,
1372, 1224, 1048, 756 cm21
;
1H NMR (200 MHz, CDCl3): d 7.46–7.31
(m, 5 H, aromatic protons), 5.22–5.18 (dd, J ¼ 5.0 and 3.2 Hz, 1H, H-4),
4.80–4.74 (dd, J ¼ 9.1 and 4.2 Hz, 1H, H-5), 4.26–4.19 (m, 2H, H-6a,b), 3.85–
3.76 (m, 1H, H-3), 3.01–2.74 (m, 2H, H-2a,b), 2.03 (s, 6H, 2 COCH3); 13C
NMR (50 MHz, CDCl3): d 170.0, 169.7, 166.6, 133.7 (2C), 132.6, 129.8 (2C),
128.9, 77.6, 67.6, 63.2, 43.2, 33.9, 20.8 (2C); ESI-MS: m/z 361 [M þ Na]þ;
Anal. Calcd. for C16H18O6S (338): C, 56.79; H, 5.36; found: C, 56.60; H, 5.60.