2,3,4-Tri-O-acetyl-1,6-anhydro-beta-D-mannopyranose, an artifact produced during carbohydrate analysis. A total synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-beta-D-mannofuranose

Carbohydr Res. 1993 Apr 23;243(1):11-27. doi: 10.1016/0008-6215(93)84078-k.

Abstract

This study confirms that 2,3,4-tri-O-acetyl-1,6-anhydro-beta-D-mannopyranose is an artifact produced during carbohydrate analysis. A new synthesis of 2,3,5-tri-O-acetyl-1,6-anhydro-beta-D-mannofuranose is also described, and a novel dimer, 1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-5,5'-di-O-(1-methox yethyl)-di - alpha-D-mannofuranose, has been isolated. The structure of the dimer is confirmed by X-ray analysis of a derivative, 1,6':6,1'-dianhydro-2,3:2',3'-di-O-isopropylidene-di-alpha-D-mannofur anose.

Publication types

  • Research Support, U.S. Gov't, Non-P.H.S.
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Artifacts*
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Mannose / analogs & derivatives*
  • Mannose / chemical synthesis
  • Mannose / chemistry
  • Models, Molecular
  • Molecular Sequence Data

Substances

  • Indicators and Reagents
  • 2,3,4-tri-O-acetyl-1,6-anhydromannopyranose
  • 2,3,5-tri-O-acetyl-1,6-anhydromannofuranose
  • Mannose