Chemical Glycosylation by Single Electron Transfer

Abstract

Oligosaccharides play important roles in nature; however, chemical synthesis of oligosaccharides is still difficult and not carried out in a fully automated manner. Among various methods, the activation of glycosyl donors by single electron transfer using electrochemical and photochemical methods has several benefits. In particular, electrochemical oxidation is a powerful method to activate glycosyl donors, including thioglycosides, which are one of the most popular class of glycosyl donors in modern chemical glycosylations. This review article covers the pioneering works of electrochemical glycosylations, other chemical glycosylations achieved by single electron transfer, and our recent approach to the automated solution-phase synthesis of oligosaccharides based on the electrochemical method.