Automated Solution-Phase Synthesis of Oligosaccharides via Iterative Electrochemical Assembly of Thioglycosides

Abstract

A new iterative one-pot sequential method for the solution-phase synthesis of oligosaccharides has been devised on the basis of the electrochemical oxidation of a propagating thioglycoside terminus to generate the corresponding triflate, followed by the reaction with a thioglycoside building block having a free hydroxyl group. A practical automated synthesizer was developed for the method and was effectively used for assembling up to six thioglycoside building blocks to synthesize partial structures of poly-β-D-(1-6)-N-acetylglucosamine.