Synthesis and characterization of the hexenuronic acid model methyl 4-deoxy-beta-L-threo-hex-4-enopyranosiduronic acid

Carbohydr Res. 2006 Oct 16;341(14):2439-43. doi: 10.1016/j.carres.2006.06.012. Epub 2006 Jul 28.

Abstract

A facile synthetic scheme for the preparation of methyl 4-deoxy-beta-L-threo-hex-4-enopyranosiduronic acid utilizing the commercially available methyl alpha-D-galactopyranoside as starting material has been developed. The synthesis sequence comprises six high yielding reaction steps: TEMPO oxidation, acetylation, methanolysis of the lactone, acetylation, beta-elimination, and final removal of the protecting groups. Only one column chromatographic purification is needed throughout the whole sequence. The overall yield is 60%. The final product has been characterized by NMR, Raman, UVRR, FTIR, and HRMS.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrate Conformation
  • Chromatography
  • Galactose / analogs & derivatives
  • Galactose / chemistry
  • Hexuronic Acids / chemical synthesis*
  • Hexuronic Acids / chemistry*
  • Magnetic Resonance Spectroscopy
  • Spectrum Analysis, Raman
  • Uronic Acids / chemical synthesis*
  • Uronic Acids / chemistry*

Substances

  • Hexuronic Acids
  • Uronic Acids
  • hexenuronic acid
  • methyl 4-deoxy-beta-L-threo-hex-4-enopyranosiduronic acid
  • methyl-galactopyranoside
  • Galactose