General synthesis of sugar-derived azepane nitrones: precursors of azepane iminosugars

J Org Chem. 2013 Apr 5;78(7):3208-21. doi: 10.1021/jo400130p. Epub 2013 Mar 11.

Abstract

A general and efficient method has been developed for the synthesis of sugar-derived azepane nitrones starting from aldohexoses, with an intramolecular condensation of aldehyde and hydroxylamine as the key step. Through this strategy, each aldohexose produced a pair of azepane nitrones, which are precursors of various azepane iminosugars.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrates / chemistry*
  • Molecular Structure
  • Nitrogen Oxides / chemical synthesis*
  • Nitrogen Oxides / chemistry

Substances

  • Carbohydrates
  • Nitrogen Oxides