Pre-activation protocol leading to highly stereoselectivity-controllable glycosylations of oxazolidinone protected glucosamines

Chem Commun (Camb). 2008 Feb 7:(5):597-9. doi: 10.1039/b712591g. Epub 2007 Nov 23.

Abstract

Under pre-activation glycosylation conditions, the 4,6-di-O-acetyl-N-acetyloxazolidinone protected donor afforded either excellent beta- or alpha-stereoselectivity simply by means of the addition of hindered base TTBP or the absence of base, leading to the controllable stereochemistry of coupling reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Glucosamine / analogs & derivatives*
  • Glucosamine / chemical synthesis*
  • Glucosamine / chemistry
  • Glycosylation
  • Oxazolidinones / chemical synthesis*
  • Oxazolidinones / chemistry
  • Stereoisomerism

Substances

  • 4,6-di-O-acetyl-N-acetyloxazolidinone
  • Oxazolidinones
  • Glucosamine