Stereoselective synthesis of 2-deoxy-beta-glycosides using anomeric O-alkylation/arylation

Org Lett. 2009 Jan 1;11(1):9-12. doi: 10.1021/ol8022006.


Anomeric O-alkylation/arylation is applied to the synthesis of 2-deoxy-beta-glycosides. Treatment of lactols with NaH in dioxane followed by the addition of electrophiles leads to the formation of 2-deoxy-beta-glycosides in high yield and high selectivity. The high beta-selectivity observed here demonstrates a powerful stereoelectronic effect for the stereoselective formation of acetals under kinetic control.

Publication types

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

MeSH terms

  • Alkylation
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry*
  • Kinetics
  • Molecular Conformation
  • Stereoisomerism


  • Glycosides