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References
15. The acceptor 2 (1 equiv.) and the glycosyl donor 1 (3.0
equiv.) were dissolved in a small quantity of toluene,
azeotroped to dryness and the mixture dried under vac-
uum overnight. The mixture was dissolved in CH2Cl2 (5
ml) at 0°C under an argon atmosphere. N-Iodosuccin-
imide (4 equiv.) was added to the solution, after stirring
for 5 min, Lewis acid was added. The reaction was
quenched after 20 min with 10% aqueous sodium thiosul-
phate and saturated aqueous sodium bicarbonate,
extracted with CH2Cl2, and purified by chromatography.
Compounds 3a, 3b and 3c were characterized by their
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1
respective H and 13C NMR spectra. NMR data for 3d:
1H NMR (400 MHz): l (CDCl3) 8.10 (d, 2H, J=7 Hz),
7.56 (t, 1H, J=7 Hz), 7.4–7.0 (m, 29H), 6.82 (d, 2H, J=8
Hz), 5.73 (t, 1H, J=2 Hz), 5.48 (d, 1H, J=1.6 Hz),
4.9–3.9 (m, 19H), 3.81 (s, 3H), 3.79–3.0 (m, 4H), 1.8–1.2
(m, 10H); 13C NMR (100 MHz): l (CDCl3) 165.94,
159.23, 139.03, 138.74, 138.48, 138.36, 138.17, 133.26,
131.36, 130.30, 130.02, 129.77, 128.74, 128.66, 128.63,
128.50, 128.48, 128.29, 128.23, 128.16, 128.06, 127.90,
127.76, 127.69, 127.55, 113.76, 111.18, 96.55, 81.18, 78.85,
78.20, 78.01, 77.62, 75.69, 75.12, 75.01, 74.01, 74.31,
74.28, 73.44, 73.35, 71.96, 71.52, 69.38, 69.16, 55.54,
37.46, 35.22, 25.25, 24.14, 23.91. Mol. mass (calcd) for
C68H72O13 1096.50, found 1096.502 (M+H).
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20. A solution of compounds 6a and 6c in CH2Cl2 treated
with BF3·Et2O (0.3 equiv.) at 0°C, the reaction was
completed in an hour. All the compounds were character-
1
ized by H and 13C NMR spectra.