1036
H. Wang et al. / Carbohydrate Research 338 (2003) 1033–1037
3.5. 2,3,5,6-Tetra-O-benzoyl-b-D-galactofuranosyl-(1
afford 1 (624 mg, 96%) as a mixture of a and b isomers
1
3)-5,6-di-O-acetyl-1,2-O-isopropylidene-a-
D-galacto-
(mainly b): [h]D +28.5° (c 0.8, H2O); H NMR (400
pyranose (8)
MHz, D2O): l 5.12, 4.96 (2 H-1); 13C NMR (100 MHz,
D2O): l 109.01 (C-1 for Galf ), 105.98 (C-1 for b-
Galp), 96.0 (C-1 for a-Galp). ESIMS: Anal. Calcd for
C12H22O11: [M] 342.3. Found: [M+H+]+ 343.2.
Compound 7 (3.8 g, 4.53 mmol) was dissolved in 90%
HOAc (100 mL). The mixture was kept at 40 °C for 4
h, and then concentrated under reduced pressure. The
resulting residue was treated with Ac2O and Py at rt for
2 h and then purified by flash chromatography (1:1
petroleum ether–EtOAc) to give 8 (3.76 g, 94% over
Acknowledgements
1
two steps): [h]D −12.2° (c 1.0, CHCl3); H NMR (400
MHz, CDCl3): l 8.10–7.23 (m, 20 H, 4 PhH), 6.15 (m,
1 H, H-5%), 5.87 (d, 1 H, J 4.1 Hz, H-1), 5.64 (d, 1 H,
J 5.0 Hz, H-3%), 5.49 (s, 1 H, H-1%), 5.42 (s, 1 H, H-2%),
5.42 (m, 1 H, H-5), 4.83 (dd, 1 H, J 3.4, 12 Hz, H-6a%),
4.77–4.72 (m, 3 H, H-2, 4%, 6b%), 4.41 (dd, 1 H, J 3.9, 12
Hz, H-6a), 4.28 (dd, 1 H, J 1.5, 6.1 Hz, H-3), 4.20 (dd,
1 H, J 7.4, 12.0 Hz, H-6b), 4.08 (dd, 1 H, J 4.4, 6.0 Hz,
H-4), 2.14, 1.96 (2 s, 6 H, C(CH3)2), 1.59, 1.38 (2 s, 6 H,
2 COCH3). Anal. Calcd for C47H46O17: C, 63.94; H,
5.25. Found: C, 63.76; H, 5.30.
This work was supported by the Beijing Natural
Science Foundation (6021004) and National Natural
Science Foundation of China (59973026 and 29905004).
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1
90%): [h]D −7.8° (c 1.0, CHCl3); H NMR (400 MHz,
CDCl3): l 8.09–7.23 (m, 20 H, 4 PhH), 6.11 (m, 1 H,
H-5%), 5.75 (s, 0.75 H, H-1% for b isomer), 5.68 (d, 0.25
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isomer), 5.48 (d, 0.75 H, J 1.1 Hz, H-2% for b isomer),
5.43 (d, 0.25 H, J 1.1 Hz, H-2% for a isomer), 5.37 (m,
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a isomer), 4.83–4.74 (m, 3 H, H-4%, 6%a, 6%b), 4.40–4.00
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Compound 9 (1.6 g, 1.90 mmol) was dissolved in an
NH3-saturated CH3OH (50 mL). After 72 h at rt, the
reaction mixture was concentrated to about 10 mL,
then CH2Cl2 (100 mL) was added. The resultant precip-
itate was filtered and washed four times with CH2Cl2 to