The 2-N,N-Dibenzylamino Group as a Participating Group in the Synthesis ofβ-Glycosides

Abstract

The novel glycosyl donor 2-N,N-dibenzylaminothioglycoside 1 reacts with glycopyranoside alcohols 2, presumably via intermediate 3, to provide 1,2-trans-linked disaccharides 4 in high yield (78-86 %) and with high stereoselectivity. The N-benzyl protecting groups are readily cleaved under normal hydrogenolysis conditions, facilitating the synthesis of oligosaccharides with free amino groups.