Glycosyl oxazolines serve as active donors for iterative synthesis of type I oligosaccharides

Abstract

Synthesis of Galβ1 → 3GlcNAc-repeating saccharides is limited mainly by the formation of less-reactive oxazolines. We herein report an expeditious approach that requires trichloroacetyloxazolines as reactive glycosyl donors. Using only two disaccharide building blocks, the iterative oxazoline formation and glycosylation synthesized hexa- and octasaccharides with overall yields of 47% and 26% in four and six steps, respectively.