N-(phenylthio)-epsilon-caprolactam: a new promoter for the activation of thioglycosides

Org Lett. 2004 Mar 4;6(5):839-41. doi: 10.1021/ol0400084.

Abstract

N-(phenylthio)-epsilon-caprolactam (1) has been applied as a new promoter for the activation of thioglycosides. This proceeds by the reaction of 1 with trifluoromethansulfonic anhydride, which subsequently activates the thioglycoside for glycosidic bond formation. Notably, the reaction proceeds efficiently at room temperature and is adaptable to our reactivity-based one-pot oligosaccharide synthesis. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Sequence
  • Glycosylation
  • Lactams / chemistry*
  • Molecular Sequence Data
  • Stereoisomerism
  • Sulfides / chemistry*
  • Thioglycosides / chemistry*

Substances

  • Lactams
  • Sulfides
  • Thioglycosides
  • N-(phenylthio)-epsilon-caprolactam