D. Mukherjee et al. / Tetrahedron 57 *2001) 7701±7704
7703
3H, J6 Hz, CH3), 2.00, 2.02, 2.03, 2.08 94s, 12H, 4Ac),
3.70 9m, 1H, C-5H), 3.94 9m 1H, O±CHr), 4.15 9m, 2H,
C-6H), 4.55 9d, 1H, J9 Hz), 4.94 9t, 1H, J9 Hz), 5.10 9t,
1H, J9.6 Hz), 5.20 9t, 1H, J9.6 Hz); dc 975 MHz, CDCl3)
170.9, 170.6, 169.9, 169.7, 100.0, 89.4, 73.3, 72.5, 72.0,
70.2, 69.0, 62.5, 23.6, 22.3, 21.1, 21.0, 21.9; FAB-MS:
m/z, 41 3 9M1Na); Anal. Calcd for C17H26O10: C, 52.30;
H, 6.60; Found: C, 52.29; H, 6.38.
1H, J9 Hz), 7.21±7.84 9m, 20H, aromatic); dc 975 MHz,
CDCl3) 170.7, 170.5, 166.6, 134.1, 133.9, 133.6, 130.3,
130.2, 130.1, 129.4, 129.1, 128.9, 128.8, 128.6, 101.5,
73.5, 71.3, 71.1, 68.9, 68.6, 67.3, 21.1, 21.0, 20.9; Anal.
Calcd for C47H46O17 S: C, 61.71; H, 5.03; Found: C,
62.01; H, 5.18.
1.1.8. Phenyl 2,3,4-tri-O-benzoyl-6-O-ꢀ2,3,4,6-tetra-O-
acetyl-b-d-mannopyranosyl)-1-thio-b-d-galactopyrano-
side ꢀ18). Sticky 988%) [a]D190 9c 0.44, CH2Cl2); Rf 0.65
[ethyl acetate/petroleum ether 91:1)]; IR 9Neat, cm21): 1734
1.1.2. Methyl 2,3,4,6-tetra-O-acetyl-b-d-glucopyrano-
side ꢀ3). Sticky974%) [a]D23.19 c 0.83, CH2Cl2); Rf 0.6
[ethyl acetate/petroleum ether 91;1)]; IR 9Neat, cm21): 1754
9ester); 1H NMR 9CDCl3): d 2.00, 2.02, 2.07, 2.09 94s, 12H,
4Ac), 3.519s, 3H, OMe), 4.44 9d, 1H, J7.8 Hz), 4.98 9t,
1H, J8.4 Hz), 5.06 9t, 1H, J9 Hz).
1
9ester), 738, 1265, 1450 9aromatic); H NMR 9CDCl3): d
2.02, 2.06, 2.09, 2.17 94s, 12H, 4Ac), 3.67 9q, J14.1Hz,
J210.5 Hz, C6HA, Gal), 3.94 9q, J17.5 Hz, J210.4 Hz),
4.08±4.34 9m, 2H, Man), 5.05 9d, 1H, J9.8 Hz), 5.58 9dd,
1H J13 Hz, J29.9 Hz, C3H, Gal), 5.76 9t, 1H,
J1J29.4 Hz, C2H, Gal), 6.09 9d, 1H J1.8 Hz,
C1HMan) 7.26±7.90 9m, 20H, aromatic); dc 975 MHz,
CDCl3) 170.9, 170.0, 169.8, 165.7, 165.5, 134.4, 133.9,
133.6, 133.5, 130.4, 130.3, 130.1, 130.1, 129.7, 129.4,
129.2, 129.1, 129.0, 128.8, 128.6, 128.3, 98.1, 91.0, 86.4,
86.0, 73.3, 71.0, 69.6, 69.4, 69.2, 68.7, 68.3, 67.4, 66.4,
66.0, 62.7, 62.5; MALDI-TOF MS: m/z, 937 9M1Na),
953 9M1K). Anal.Calcd for C47H46O17S: C, 61.71; H,
5.03; Found: C, 62.00; H, 5.11.
1.1.3. Benzyl 2,3,4,6-tetra-O-acetyl-b-d-glucopyranoside
ꢀ5). Sticky 968%) [a]D153.7 9c 0.96, CH2Cl2); Rf 0.5
[ethyl acetate/petroleum ether 91;1)]; IR 9Neat, cm21):
1
1739 9ester), 743, 1246 9aromatic); H NMR 9CDCl3): d
1.99, 2.00, 2.08, 2.09 94s, 12H, 4Ac), 3.64±3.69 9m, 1H,
H-5), 4.55 9d, 1H, J7.8 Hz), 7.27±7.35 9m, 5H, aromatic).
1.1.4. Allyl 2,3,4,6-tetra-O-acetyl-b-d-glucopyranoside
ꢀ10). Sticky 962%) [a]D162.6 9c 0.43, CH2Cl2); Rf 0.6
[ethyl acetate/petroleum ether 91;1)]; IR 9Neat, cm21):
1
1.1.9. Benzyl 2-deoxy-3,4,6-tri-O-acetyl-2-phthalimido-
b-d-glucopyranoside ꢀ20). Sticky 990%) [a]D27.19 c
0.75, CHCl3); Rf 0.42 [ethyl acetate/petroleum ether
91:1)]; IR 9KBr, cm21): 1750 9ester), 1716 9imide), 721
1733 9ester), H NMR 9CDCl3): d 1.98, 2.05, 2.06, 2.1,
94s, 12H, 4Ac), 4.5 9d, 1H, J7 Hz), 5.85 9m, 1H,
CH2vCH).
1
9aromatic); H NMR 9CDCl3): d 1.85, 2.02, 2.13 93s, 9H,
1.1.5. 1,2:5,6-Di-O-isopropylidene-3-O-ꢀ2,3,4,6-tetra-O-
acetyl-b-d-glucopyranosyl)-a-d-glucofuranose
3Ac), 3.85±3.89 9H-5), 4.53 9d, 1H, J12.3 Hz), 4.85 9d,
1H, J12.0 Hz), 5.18 9t, J2,3J3,49 Hz, H-3), 5.37 9d, 1H,
J9 Hz), 5.78 9t, 1H, J3,4J4,59 Hz, H4), 7.26±7.38 9m,
4H, Phthaloyl-H), 7.72±7.85 9m, 5H, aromatic); dc
975 MHz, CDCl3), 171.0, 170.4, 169.8, 167.8, 137.0,
134.8, 134.5, 131.8, 128.6, 128.2, 128.1, 123.9, 97.6, 72.2,
71.7, 69.5, 62.4, 55.0, 21.1, 20.9, 20.8; FAB-MS: m/z, 548
9M1Na); Anal.Calcd for C27H27O10N: C, 61.71; H, 5.14; N,
2.67; Found: C, 61.69; H, 5.11; N, 2.66.
ꢀ12).
Sticky969%) [a]D168.5 9c 0.40, CH2Cl2); Rf 0.6 [ethyl
acetate/petroleum ether 91:1)]; IR9Neat, cm21): 1748
9ester); H NMR 9CDCl3): d 1.32 9s, 3H), 1.34 9s, 3H),
1
1.36 9s, 3H), 1.49 9s, 3H), 2.04, 2.05, 2.09, 2.10 94s, 12H,
4Ac), 4.94 9t, 1H, J4 Hz), 5.00 9d, 1H, J4.2 Hz), 5.03 9d,
1H, J4 Hz), 5.56 9t, 1H, J9.6 Hz), 5.95 9d, J3 Hz,
C-1H, furan), 6.29 9d, J6 Hz); dc 975 MHz, CDCl3)
169.8, 169.3, 90.1, 70.8, 70.4, 69.5, 61.1, 23.8, 22.9, 22.6;
MALDI-TOFMS: m/z, 61 3 9M1Na), 629 9M1K). Anal.
Calcd for C26H38O15: C, 52.88;H, 6.44; Found: C, 52.91;
H, 6.51.
Acknowledgements
The ®nancial assistance of DST, India to U. S. C. is grate-
fully acknowledged.
1.1.6. 1,2:3,4-Di-O-isopropylidene-6-O-ꢀ2,3,4,6-tetra-O-
acetyl-b-d-glucopyranosyl)-a-d-galactopyranose ꢀ14).
Sticky 978%) [a]D220 9c 1.56, CH2Cl2); Rf 0.6 [ethyl
acetate/petroleum ether 91:1)]; IR 9Neat, cm21): 1754
1
9ester,); H NMR 9CDCl3): d 1.32 9s, 3H), 1.44 9s, 3H),
References
1.50 9s, 3H), 1.98, 2.00, 2.06, 2.09 94s, 12H, 4Ac), 4.02
9dd, 1H, J13.4 Hz, J211.4 Hz) 5.19 9d, 1H, J9.5 Hz),
5.49 9d, 1H); dc 975 MHz, CDCl3) 170.5, 169.5, 169.4,
169.3, 101.4, 96.3, 71.7, 70.6, 69.8, 69.4, 65.9, 63.4, 61.9,
61.4, 25.0, 24.4, 24.3, 22.6, 20.7, 20.6, 20.5; MALDI-
TOFMS: m/z, 61 3 9M1Na), 629 9M1K). Anal Calcd for
C26H38O15: C, 52.88, 6.44; Found: C, 52.90; H, 6.49.
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