Isomerisation of aldoses in pyridine in the presence of aluminium oxide

Carbohydr Res. 2005 Feb 28;340(3):373-7. doi: 10.1016/j.carres.2004.12.006.

Abstract

Addition of aluminium oxide to boiling pyridine solutions of D-xylose, L-arabinose, D-mannose and D-glucose strongly increased the reaction rate of the aldose-ketose transformation. The maximum content of 2-ketose was reached after less than 2h for the aldopentoses and 3h for the aldohexoses. D-Threo-2-pentulose (xylulose) was prepared from D-xylose, and isolated as its O-isopropylidene derivative, the yield was nearly twice that compared to that usually obtained in the classical Lobry de Bruyn-Alberda van Ekenstein transformation in pyridine.

MeSH terms

  • Aluminum Oxide / chemistry*
  • Isomerism
  • Monosaccharides / chemistry*
  • Pyridines / chemical synthesis
  • Pyridines / chemistry*

Substances

  • Monosaccharides
  • Pyridines
  • Aluminum Oxide
  • pyridine