Synthesis from D-altrose of (5R,6R,7R,8S)-5,7-dihydroxy-8-hydroxymethylconidine and 2,4-dideoxy-2,4-imino-D-glucitol, azetidine analogues of swainsonine and 1,4-dideoxy-1,4-imino-D-mannitol

Org Lett. 2012 Aug 17;14(16):4174-7. doi: 10.1021/ol301844n. Epub 2012 Jul 27.

Abstract

Ring closure of a 3,5-di-O-triflate derived from D-altrose with benzylamine allowed the formation of both monocyclic and bicyclic azetidine analogues of swainsonine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azetidines / chemical synthesis*
  • Azetidines / chemistry
  • Cyclization
  • Hexoses / chemistry*
  • Imino Furanoses / chemical synthesis
  • Imino Furanoses / chemistry
  • Mannitol / analogs & derivatives*
  • Mannitol / chemical synthesis
  • Mannitol / chemistry
  • Mannosidases / antagonists & inhibitors
  • Molecular Structure
  • Polymers / chemical synthesis*
  • Polymers / chemistry
  • Sorbitol / analogs & derivatives
  • Structure-Activity Relationship
  • Swainsonine / analogs & derivatives*
  • Swainsonine / chemical synthesis*
  • Swainsonine / chemistry

Substances

  • (5R,6R,7R,8S)-5,7-dihydroxy-8-hydroxymethylconidine
  • 2,4-dideoxy-2,4-imino-D-glucitol
  • Azetidines
  • D-altrose
  • Hexoses
  • Imino Furanoses
  • Polymers
  • azetidine
  • Mannitol
  • Sorbitol
  • 1,4-dideoxy-1,4-iminomannitol
  • Mannosidases
  • Swainsonine