Rapid oligosaccharide synthesis using a fluorous protective group

J Org Chem. 2004 Aug 6;69(16):5348-53. doi: 10.1021/jo049425k.

Abstract

The Bfp-OH, a novel fluorous protecting reagent, was able to be easily prepared. The Bfp group was readily introduced to a carbohydrate, removed in high yield, and recyclable after cleavage. The use of the Bfp group made it possible to synthesize a pentasaccharide by minimal column chromatography purification. Each synthetic intermediate was able to be easily purified only by simple fluorous-organic solvent extraction and monitored by TLC, NMR, and MS.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chromatography, Thin Layer
  • Fluorine / chemistry*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Oligosaccharides / chemical synthesis*
  • Protective Agents / chemistry*

Substances

  • Indicators and Reagents
  • Oligosaccharides
  • Protective Agents
  • Fluorine