Regio- and stereoselective anomeric esterification of glucopyranose 1,2-diols and a facile preparation of 2-O-acetylated glucopyranosyl trichloroacetimidates from the corresponding 1,2-diols

Abstract: A highly regio- and stereoselective anomeric esterification of 3-O-allyl (or benzyl, or benzoyl)-4,6-O-isopropylidene-α,β-d-glucopyranose with acetyl chloride, or allyl chloroformate, or ethyl chloroformate gave the corresponding 2-OH, 1-β-acetates or -carbonates in excellent yields. The 2-OH, 1-β-acetates were readily converted to the corresponding 2-O-acetylated glucopyranosyl trichloroacetimidates by reaction with trichloroacetonitrile via base promoted acetyl migration, while the 2-OH, 1-β-carbonates were good glycosyl acceptors for the synthesis of (1→2)-linked oligosaccharides. [Copyright &y& Elsevier]