BF3 ⋅ CH3CN Promotes a Formation of Aryl α‐O‐Glycosides from Pyranoses: A Facile Approach to Oligosaccharide EPS‐G7

Abstract

AbstractA BF3 ⋅ CH3CN‐promoted synthesis of aryl α‐O‐glycosides from readily available glycosyl donors was developed. This reaction could proceed well on a gram‐scale under mild condition with α/β ratio up to 95 : 5. Moreover, a variety of the glycosyl donors including acetylated/benzoylated pyranoses, di‐ and trisaccharide derivatives as well as glycosyl acceptors from substituted phenols, sterically hindered aliphatic alcohols and carboxylic acid, were well tolerant. Importantly, the potential of this strategy was highlighted with a successful gram‐scale synthesis of oligosaccharide EPS‐G7, which is a commercial detection reagent for quantitative determination of α‐amylase.