Studies on Glycosylation. III. A Novel, Stereospecific Synthesis of 1-O-Acyl- and 1-Aryl-β-D-glucopyranose Tetraacetates via the 1, 2-t-Butyl-orthoacetate

Abstract

1-O-Acyl-β-D-glucopyranose tetraacetates (I-IX) were obtained in high yields by the condensation of acetylated α-D-glucopyranose 1, 2-(t-butyl orthoacetate) with carboxylic acids in chlorobenzene under reflux. The similar reaction with some phenols and p-nitrothiophenol provided the corresponding aryl-β-D-glucoside derivatives (X-XII).