Diastereo- and enantioselective synthesis of 1'-C-branched N,O-nucleosides

Nucleosides Nucleotides Nucleic Acids. 2003 May-Aug;22(5-8):739-42. doi: 10.1081/NCN-120022623.

Abstract

A synthetic approach towards 1'-C-branched N,O-nucleosides is reported, based on 1,3-dipolar cycloaddition of ethoxycarbonylnitrone. The asymmetric version of the process exploits the presence of a chiral auxiliary at the carbon atom of nitrone and leads to beta-D and beta-L nucleosides in good yields.

MeSH terms

  • Indicators and Reagents
  • Models, Molecular
  • Molecular Conformation
  • Nitrogen Oxides / chemistry*
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry*
  • Stereoisomerism

Substances

  • Indicators and Reagents
  • Nitrogen Oxides
  • Nucleosides
  • ethoxycarbonylnitrone
  • nitrones