Synthesis of urea-tethered neoglycoconjugates and pseudooligosaccharides in water

J Am Chem Soc. 2006 Mar 29;128(12):3934-8. doi: 10.1021/ja056253f.

Abstract

A novel approach to the synthesis of urea glycosides in aqueous media has been explored. Steyermark's glucopyranosyl oxazolidinone was found to be a good synthon for anchoring glucosyl moieties onto amines and thiols. The present method was successfully applied to establish a new route for the synthesis of urea-tethered neoglycoconjugates and pseudooligosaccharides in water.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry
  • Carbohydrate Sequence
  • Glycoconjugates / chemical synthesis*
  • Glycosides / chemical synthesis
  • Glycosides / chemistry
  • Molecular Sequence Data
  • Oligosaccharides / chemical synthesis*
  • Oxazolidinones / chemistry
  • Sulfhydryl Compounds / chemistry
  • Urea / analogs & derivatives
  • Urea / chemical synthesis
  • Urea / chemistry*
  • Water / chemistry

Substances

  • Amines
  • Glycoconjugates
  • Glycosides
  • Oligosaccharides
  • Oxazolidinones
  • Sulfhydryl Compounds
  • Water
  • Urea