Novel synthesis of the glycosidase inhibitor deoxymannojirimycin and of a synthetic precursor D-lyxo-hexos-5-ulose

Org Lett. 2001 Oct 18;3(21):3353-6. doi: 10.1021/ol016596s.

Abstract

[reaction: see text]. The synthesis of D-lyxo-hexos-5-ulose (5-ketomannose, 1,5-dicarbonyl sugar), a synthetic precursor to the glycoprocessing inhibitor deoxymannojirimycin, was carried out by an in situ epoxidation and hydrolysis of a trimethylsilyl-protected 6-deoxyhex-5-enopyranoside followed by facile removal of the protecting groups. A novel nine-step synthesis of deoxymannojirimycin has also been achieved from methyl alpha-D-mannopyranoside; this involved methanolysis of epoxides derived from an acetylated 1-azido-6-deoxyhex-5-enopyranoside followed by deprotection and catalytic hydrogenation.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 1-Deoxynojirimycin / chemical synthesis*
  • Anti-Bacterial Agents / chemical synthesis
  • Antiviral Agents / chemical synthesis
  • Chemistry, Pharmaceutical
  • Enzyme Inhibitors / chemical synthesis*
  • Epoxy Compounds / chemistry
  • Glycoside Hydrolases / antagonists & inhibitors*
  • Mannose / analogs & derivatives
  • Mannose / chemical synthesis*
  • Methylmannosides / chemistry

Substances

  • 5-ketomannose
  • Anti-Bacterial Agents
  • Antiviral Agents
  • Enzyme Inhibitors
  • Epoxy Compounds
  • Methylmannosides
  • 1-Deoxynojirimycin
  • methylmannoside
  • Glycoside Hydrolases
  • Mannose