Synthesis of a versatile (S)-3-(hydroxymethyl)butane-1,2,4-triol building block and its application for the stereoselective synthesis of N-homoceramides

Org Lett. 2005 Dec 22;7(26):5769-72. doi: 10.1021/ol052335x.

Abstract

[structures: see text] A versatile (S)-3-(hydroxymethyl)butane-1,2,4-triol building block has been synthesized starting from D-isoascorbic acid, a common food preservative. The key transformation in this approach was the introduction of branching through a high yield and fully regioselective epoxide opening. This flexible synthon has been elaborated to a new class of (dihydro-)N-homo(phyto)ceramides.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ascorbic Acid / chemistry*
  • Butanols / chemical synthesis*
  • Butanols / chemistry
  • Catalysis
  • Ceramides / chemical synthesis*
  • Ceramides / chemistry
  • Food Preservatives / chemistry*
  • Indicators and Reagents
  • Molecular Structure
  • Stereoisomerism

Substances

  • (S)-3-(hydroxymethyl)butane-1,2,4-triol
  • Butanols
  • Ceramides
  • Food Preservatives
  • Indicators and Reagents
  • isoascorbic acid
  • Ascorbic Acid