Dimethylthexylsilyl 2-acetamido-3-O-allyl-2-deoxy-6-O-(4-methoxybenzyl)-β-d-glucopyranoside, dimethylthexylsilyl 3,4,6-tri-O-benzyl-β-d-mannopyranosyl-(1→4)-2-acetamido-3-O-allyl-2-deoxy-6-O-(4-methoxybenzyl)-β-d-glucopyranoside, and dimethylthexylsilyl 2-O-(benzylsulfonyl)-3,4,6-tri-O-benzyl-β-d-mannopyranosyl-(1→4)-2-acetamido-3-O-allyl-2-deoxy-6-O-(4-methoxybenzyl)-β-d-glucopyranoside: synthesis of authentic samples

摘要

Dimethylthexylsilyl 2-acetamido-3-O-allyl-2-deoxy-6-O-(4-methoxybenzyl)-beta-D-glucopyranos ide was prepared by reduction of the corresponding 4,6-O-(4-methoxybenzylidene) acetal with sodium cyanoborohydride and trifluoroacetic acid. This alcohol was coupled to 2-O-benzoyl-3,4,6-tri-O-benzyl-alpha-D-glucopyranosyl trichloroacetimidate to give a beta-glucoside that was converted to dimethylthexylsilyl 3,4,6-tri-O-benzyl-beta-D-mannopyranosyl-(1 -> 4)-2-acetamido-3-O-allyl-2-deoxy-6-O-(4-methoxybenzyl)-beta-D-glucopyra noside by saponification, Dess-Martin oxidation, and sodium borohydride reduction. Sulfonylation then gave dimethylthexylsilyl 2-O-(benzylsulfonyl)-3.4,6-tri-O-benzyl-beta-D-mannopyranosyl-(1 -> 4)-2-acetamido-3-O-allyl-2-deoxy-6-O-(4-methoxybenzyl)-beta-D-glucopyra noside. (C) 2008 Elsevier Ltd. All rights reserved