Stereocontrolled Synthesis of Phenolic α-d-Glycopyranosides

Dedicated to Professor Richard Schmidt for his seminal contributions to glycoside synthesis

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.

Key words

aryl glycoside - stereocontrolled glycosidation - minimal protection - 1,2-cis d-glycopyranoside - phenyl sialoside

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