Synthesis of new amino sugar derivatives from keto-sugars of D-xylose

Carbohydr Res. 2006 Oct 16;341(14):2312-20. doi: 10.1016/j.carres.2006.06.018. Epub 2006 Jul 25.

Abstract

Several amino sugars and imino sugar derivatives were synthesized from keto-sugars of D-xylose through a series of reactions such as the Henry reaction, hydrogenation reactions, and nucleophilic addition reactions or substitution reactions. Thiazine derivative 15 was obtained by the reaction of the keto-sugar with NH(2)CSNH(2). Higher carbon sugar 16 was accidentally prepared at room temperature from the keto-sugar in the presence of NH(2)CONH(2). The structures of the compounds were confirmed by spectral analysis. The absolute configurations of all asymmetric carbon atoms of 6 and 8 were confirmed by X-ray crystallographic analysis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Sugars / chemical synthesis*
  • Amino Sugars / chemistry*
  • Carbohydrate Conformation
  • Carbohydrate Sequence
  • Crystallography, X-Ray
  • Imino Sugars
  • Ketoses / chemistry*
  • Molecular Structure
  • Stereoisomerism
  • Xylose / chemistry*

Substances

  • Amino Sugars
  • Imino Sugars
  • Ketoses
  • Xylose