Reaction Steps
By use of general procedure B, 2-nitrobenzyl 2,3-bis(3,4,5-tris(benzyloxy)benzoyl)-β-D-glucopyranoside (2.10 g, 1.81 mmol) was coupled with 3-tert-butyldimethylsiloxy-4,5-diphenylmethylenedioxybenzoic acid (1.62 g, 3.62 mmol) to afford 2.99 g (80%) of 2-nitrobenzyl 4,6-bis(3-tert-butyldimethylsiloxy-4,5-diphenylmethylenedioxybenzoyl)-2,3-bis(3,4,5-tris(benzyloxy)benzoyl)-β-D-glucopyranoside as a white solid foam following flash column chromatography using 10%, and then 20%, EtOAc in hexanes as eluent. IR (CH2Cl2) 1729 cm−1; 1H NMR (CDCl3, 75 MHz) δ 8.05 (d, J=1.3 Hz, 1H), 7.98 (d, J=4 Hz, 1H), 7.70-7.15 (m, 60H), 5.84 (t, J=9.7 Hz, 1H), 5.67-5.56 (m, 2H), 5.31 (d, J=15.2 Hz, 2H), 5.13-4.89 (m, 14H), 4.64, (d, J=10.6 Hz, 1H), 4.38-4.32 (m, 1H), 4.15-4.12 (m, 1H), 0.99 (s, 9H), 0.96 (s, 9H) 0.19 (s, 6H), 0.18 (s, 6H); 13C NMR (CDCl3, 75 MHz) δ 165.6, 165.3, 164.9, 164.4, 152.5, 148.6, 146.8, 142.8, 142.0, 141.7, 139.9, 139.6, 138.6, 137.4, 136.5, 133.7, 129.2, 128.9, 128.4, 128.3, 128.1, 128.0, 127.6, 127.5, 126.2, 124.6, 124.2, 124.0, 123.5, 122.5, 119.1, 118.8, 118.2, 109.3, 109.1, 104.1, 100.1, 75.1, 75.0, 73.3, 72.8, 72.3, 71.2, 71.1, 68.9, 68.3, 62.5, 26.05, 26.04, 18.3, 18.2, −4.0; MS (+FAB) 2020 (MH+, 23). Anal. Calcd for Cl21H113NO24Si2: C, 71.92; H. 5.59; N, 0.69; Found: C, 72.16; H, 5.80: N, 0.58.
