Chapter 4: A Sugar Machine¹

A sugar machine for the automated electrochemical solution-phase synthesis of oligosaccharides has been developed. The machine enables the quantitative conversion of thioglycosides into glycosyl triflates that are highly reactive glycosylation intermediates and glycosylation reaction with thioglycosides as coupling partners. This one-pot process of chemical glycosylation can be repeated for multiple cycles until the target oligosaccharide is obtained. Total syntheses of biologically active oligosaccharides have been achieved by using the sugar machine.