2856
S. Mukherjee, B. Mukhopadhyay
LETTER
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(29) p-Methoxyphenyl 2,3-Di-O-benzoyl-4,6-O-benzylidene-
b-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-
b-D-glucopyranoside (26): 1H NMR (CDCl3, 500 MHz):
d = 7.87, 7.83 (2 × d, 4 H, ArH), 7.38–7.13 (m, 21 H, ArH),
6.87, 6.68 (2 × d, 4 H, ArH), 5.67 (t, J = 9.5 Hz, 1 H, H-3¢),
5.47 (s, 1 H, CHPh), 5.42 (d, J = 3.0 Hz, 1 H, H-4), 5.38 (dd,
J = 8.0, 9.5 Hz, 1 H, H-2¢), 5.17 (d, J = 8.0 Hz, 1 H, H-1¢),
4.76 (d, J = 8.0 Hz, 1 H, H-1), 4.68 (d, J = 10.5 Hz, 1 H,
CH2Ph), 4.44, 4.40 (2 × d, J = 10.5 Hz, 2 H, CH2Ph), 4.30 (d,
J = 10.5 Hz, 1 H, CH2Ph), 4.29 (m, 1 H, H-6a¢), 3.92 (dd,
J = 4.0, 9.5 Hz, 1 H, H-3), 3.89 (t, J = 9.5 Hz, 1 H, H-4¢),
3.78 (m, 2 H, H-2, H-6b¢), 3.68 (m, 2 H, H-4¢, H-6a), 3.67 (s,
3 H, ArCH3), 3.52 (m, 3 H, H-5, H-5¢, H-6b), 2.11 (s, 3 H,
COCH3). 13C NMR (CDCl3, 500 MHz): d = 170.4 (COCH3),
165.6, 165.1 (2 × COPh), 155.4, 151.3, 137.8, 136.8, 133.3,
133.2, 129.8, 129.7, 129.4, 129.3 (2), 129.0, 128.5 (2), 128.4
(2), 128.3 (2), 128.2 (2), 128.0(2), 127.9 (2), 127.8 (2), 127.7
(2), 126.1 (2), 118.3 (2), 114.6 (2) (ArC), 102.7 (CHPh),
101.4 (C-1¢), 101.1 (C-1), 79.4, 78.6, 76.2, 75.1, 73.8, 73.0,
71.9, 69.7, 68.7, 68.6, 66.5, 55.6 (ArCH3), 20.8 (COCH3).
HRMS: m/z calcd for C56H54O15Na [M + Na]+: 989.3360;
found: 989.3354.
(30) General procedure for glycosylation reactions: A mixture of
acceptor (1.0 mmol), thioglycoside donor (1.2 mmol) and
4 Å MS in anhydrous CH2Cl2 (10 mL) was stirred under
nitrogen for 30 min. La(OTf)3 (0.3 mmol) was added and the
mixture was stirred at 0 °C until TLC (n-hexane–EtOAc,
2:1) showed complete consumption of the starting material.
The mixture was filtered through a pad of Celite and the
filtrate was washed successively with aq Na2S2O7
(2 × 20 mL), aq sat. NaHCO3 (2 × 20 mL), and brine (20
mL). The organic layer was separated, dried (Na2SO4),
filtered and evaporated in vacuo. The residue was purified
by flash chromatography using a suitable mixture of
n-hexane–EtOAc as eluent to afford pure glycosylated
products.
(20) Dasgupta, S.; Rajput, V. K.; Roy, B.; Mukhopadhyay, B.
J. Carbohydr. Chem. 2007, 26, 91.
(21) Schmidt, R. R.; Michel, J. Angew. Chem. 1980, 92, 763.
(22) Konradsson, P.; Mootoo, D. R.; McDevitt, R. E.; Fraser-
Reid, B. J. Chem. Soc., Chem. Commun. 1990, 270.
Synlett 2010, No. 19, 2853–2856 © Thieme Stuttgart · New York