Glycosyl transfer to nitrogen via cycloaddition

Org Lett. 1999 Jul 15;1(1):111-3. doi: 10.1021/ol990583l.

Abstract

[formula: see text] This letter describes the reduction to practice of a novel concept for functionalization of the anomeric carbon of carbohydrates with a nitrogen substituent. Thus, bisheterodienes with a thiono sulfur terminus and a sulfonylimine terminus are shown to undergo cycloaddition smoothly and stereoselectively to three different glycals.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Glucosides / chemical synthesis*
  • Glycosylation
  • Nitrogen / chemistry*
  • Stereoisomerism
  • Sulfur / chemistry

Substances

  • Glucosides
  • Sulfur
  • Nitrogen