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


  • Financial support from the National Institute of General Medical Sciences (R01GM090000), the Searle Scholars Program, Shanghai Committee of Science and Technology (11DZ2260600, Shanghai Municipal Education Commission Fellowship to J.Z.), and Yale University is gratefully acknowledged. We thank Dr. Seann Mulcahy for preliminary experiments and Dr. Le Li for helpful discussions.


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