A direct and stereospecific approach to the synthesis of alpha-glycosyl thiols

Org Biomol Chem. 2008 Jun 21;6(12):2061-3. doi: 10.1039/b804536d. Epub 2008 Apr 30.

Abstract

A new simple method for the synthesis of alpha-glycosyl thiols is described. Ring-opening of 1,6-anhydrosugars with commercially available bis(trimethylsilyl)sulfide under the action of catalytic amounts of TMSOTf smoothly afforded alpha-glycosyl thiols in very high yields and in a stereospecific way.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Mesylates / chemistry
  • Stereoisomerism
  • Sulfhydryl Compounds / chemical synthesis*
  • Trimethylsilyl Compounds / chemistry

Substances

  • Mesylates
  • Sulfhydryl Compounds
  • Trimethylsilyl Compounds
  • trimethylsilyl trifluoromethanesulfonate