Direct synthesis of β-N-glycosides by the reductive glycosylation of azides with protected and native carbohydrate donors

Angew Chem Int Ed Engl. 2013 Jun 3;52(23):6068-71. doi: 10.1002/anie.201301264. Epub 2013 Apr 22.

Abstract

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).

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides / chemistry*
  • Carbohydrates / chemistry*
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Glycosylation

Substances

  • Azides
  • Carbohydrates
  • Glycosides