Preparation of benzyl 2-benzyloxycarbonylamino-4-dichloroacetamido-2,4-dideoxy-alpha- D-xylopyranoside, substrate for the synthesis of the heterocyclic analogue of chloromycetin

Rocz Akad Med Bialymst. 1997;42(1):114-28.

Abstract

The paper describes the eleven stage synthesis of the derivative (XI) of 2,4-diamino-2,4-dideoxy-D-xylose, containing amino groups selectively substituted by two different acyls. The initial substrate was L-arabinose. The compound obtained, after removing the blocking groups, constitutes a semiproduct for the synthesis of the pyrrole analogue of chloromycetin by the Knorr method.

MeSH terms

  • Acylation
  • Amino Sugars / chemical synthesis*
  • Amino Sugars / chemistry
  • Anti-Bacterial Agents / chemical synthesis*
  • Arabinose / analogs & derivatives
  • Arabinose / chemistry
  • Chemistry, Pharmaceutical
  • Chloramphenicol / analogs & derivatives*
  • Chloramphenicol / chemical synthesis
  • Chromatography, Thin Layer
  • Deoxy Sugars / chemistry
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Pyrroles / chemical synthesis
  • Spectrophotometry, Infrared
  • Xylose / analogs & derivatives
  • Xylose / chemistry

Substances

  • 2,4-diamino-2,4-dideoxyxylose
  • Amino Sugars
  • Anti-Bacterial Agents
  • Deoxy Sugars
  • Pyrroles
  • benzyl 2-benzyloxycarbonylamino-4-dichloroacetamido-2,4-dideoxyxylopyranoside
  • Chloramphenicol
  • Xylose
  • Arabinose