Syntheses of amphiphilic glycosylamides from glycosyl azides without transient reduction to glycosylamines.

@article{Boullanger2000SynthesesOA,
  title={Syntheses of amphiphilic glycosylamides from glycosyl azides without transient reduction to glycosylamines.},
  author={Paul Boullanger and Val{\'e}rie Maunier and Dominique Lafont},
  journal={Carbohydrate research},
  year={2000},
  volume={324 2},
  pages={
          97-106
        }
}
Protected glycosyl azides react with acyl chlorides in the presence of triphenylphosphine to afford glycosylamides in high yields, at room temperature. Starting from the beta-glycosyl azides, the reaction is highly stereoselective and occurs with retention of configuration, whereas the alpha-azido anomers display a lower stereoselectivity giving rise to alpha/beta mixtures of glycosylamides. The reaction was applied to several monosaccharidic azides and to lactosyl azide with various acyl… CONTINUE READING