A survey of Ley's reactivity tuning in oligosaccharide synthesis

Abstract

This chapter summarizes the concepts and chemistry developed by Ley's group in relation to the relevance of reactivity tuning in oligosaccharide coupling reactions. The recognition that protecting groups affect the reactivity of glycosyl donors allowed Ley's group to make imaginative use of their 1,2-diacetal protecting groups. The combination of 1,2-diacetals with the presence of different anomeric leaving groups provides up to four different levels of reactivity. The exploitation of these reactivity levels in chemoselective glycosylation processes (reactivity tuning) has allowed the development of highly simplified routes to several complex oligosaccharides in step-wise or one-pot procedures.