A versatile route to L-hexoses: synthesis of L-mannose and L-altrose

Org Lett. 2006 Oct 12;8(21):4863-6. doi: 10.1021/ol061916z.

Abstract

[reaction: see text] An efficient route for the synthesis of orthogonally protected l-sugars has been opened up, starting from the heterocyclic homologating agent 1 and 2,3-O-isopropylidene-l-glyceraldehyde (2). Our synthetic path enables the synthesis of a 2,3-unsaturated-l-pyranoside, which can be suitably functionalized to afford the desired l-hexoses. In this paper, we report the synthesis of l-manno- and l-altro-pyranosides. Moreover, this strategy may be used to prepare all eight sugars and their derivatives in either enantiomeric form.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Hexoses / chemical synthesis*
  • Hexoses / chemistry
  • Mannose / analogs & derivatives*
  • Mannose / chemical synthesis*
  • Mannose / chemistry
  • Molecular Structure
  • Stereoisomerism

Substances

  • Hexoses
  • Mannose