Stereocontrolled Synthesis of Phenolic α-d-Glycopyranosides

Abstract

Adopting the ‘remote activation concept’ toward stereocontrolled glycoside synthesis with minimal use of protection groups, a general synthesis of phenolic 1,2- cis glycopyranosides is reported, as exemplified by aryl α- d -galacto-, α- d -gluco- and 2-azido α- d -glucopyranosides among others using glycosyl donors bearing an anomeric (3-bromo-2-pyridyloxy) group and catalyzed by methyl triflate.