Direct Synthesis of [beta]-N-Glycosides by the Reductive Glycosylation of Azides with Protected and Native Carbohydrate Donors

A simple and straightforward method for the stereocontrolled synthesis of [beta]-linked N-glycosides uses alkyl and aryl azides as the nitrogen source. The N-glycosides are formed in high yields and with high [beta] selectivities (typically >70% yield, >15:1 [beta]:α selectivity). This approach is also amenable to the synthesis of N-glycosylated amino acids and peptides (see example, Fmoc=9-fluorenylmethoxycarbonyl).