Studies on glycosylation. III. A novel, stereospecific synthesis of 1-O-acyl- and 1-aryl-.BETA.-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).