A Convergent Synthetic Strategy towards Oligosaccharides containing 2,3,6-Trideoxypyranoglycosides

Abstract

A de novo synthetic strategy for the production of oligosaccharides containing 2,3,6-trideoxypyranoglycoside is reported. The key event is the Pd-catalyzed asymmetric diastereoselective hydroalkoxylation of ene-alkoxyallene-linked glycosidic fragments. The utility of this approach was demonstrated by the activation-free, stereodivergent, and convergent synthesis of various 2-deoxyoligosaccharides, as well as their aglycon conjugates.

Keywords: asymmetric synthesis; carbohydrates; diastereoselectivity; oligosaccharides; palladium.