Electrochemical Methods as Enabling Tools for Glycosylation

Abstract Electrochemical methods have been widely used for organic synthesis including glycosylation. Electrochemical oxidation via single electron transfer (SET) is a powerful method to activate various types of glycosyl donors. Their oxidation potentials, which reflect the reactivity of glycosyl donors under anodic oxidation conditions are tunable by changing protecting groups and the anomeric leaving groups of glycosyl donors. Not only thioglycosides but also other chalcogenoglycosides have been studied as highly reactive glycosyl donors. Recently, automated electrochemical assembly, which is an automated electrochemical solution‐phase synthesis of oligosaccharides was successfully demonstrated by the rational optimization of thioglycosides as both glycosyl donors and acceptors through electrochemical measurements and DFT calculations.

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