FeCl3-catalyzed alpha-glycosidation of glycosamine pentaacetates

Carbohydr Res. 2008 Dec 8;343(18):3096-9. doi: 10.1016/j.carres.2008.09.003. Epub 2008 Sep 9.

Abstract

An efficient method for the large-scale preparation of alpha-N-acetylglycosaminides, such as fluorogenic T(N)-antigen probes and an alpha-GalNAc-Ser derivative, has been achieved using FeCl(3)-catalyzed one-step condensation between commercially available D-glycosamine pentaacetates and fluorogenic acceptors (or serine acceptor) in refluxing 1,2-dichloroethane. Experimental simplicity, high alpha-stereoselectivity, low cost, satisfactory yield, and the environmentally benign nature are major advantages of our approach.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetylglucosamine / chemistry*
  • Catalysis
  • Chlorides
  • Costs and Cost Analysis
  • Ferric Compounds / chemistry*
  • Glycosides / chemistry*
  • Green Chemistry Technology
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Chlorides
  • Ferric Compounds
  • Glycosides
  • ferric chloride
  • Acetylglucosamine