Synthesis of sugar-lactams from azides of glucuronic acid

Carbohydr Res. 2007 Sep 3;342(12-13):1953-9. doi: 10.1016/j.carres.2007.04.003. Epub 2007 Apr 18.

Abstract

Sugar-lactams have found application as glycosidase inhibitors, synthetic precursors of iminosugars and they are structural components of natural products. The synthesis of beta-D-glucopyranosidurono-6,1-lactams from glucuronic acid derivatives are described. NMR data and X-ray crystal structures indicate that the sugar-lactams adopt distorted (1)C4 conformations in solution and in the solid state.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides*
  • Carbohydrate Conformation
  • Carbohydrates / chemical synthesis
  • Carbohydrates / chemistry
  • Glucosides / chemistry
  • Glucuronic Acid / chemistry*
  • Lactams / chemical synthesis*
  • Lactams / chemistry
  • Models, Molecular

Substances

  • Azides
  • Carbohydrates
  • Glucosides
  • Lactams
  • Glucuronic Acid