A general route to D- and L-six-membered nucleoside analogues

Nucleosides Nucleotides Nucleic Acids. 2007;26(8-9):959-62. doi: 10.1080/15257770701508166.

Abstract

A simple synthetic route for novel L-(as well as D-) six-membered nucleosides is described. Particularly, we have provided a general approach to the synthesis of azasugar-based nucleosides, which preparation has been easily achieved starting from the coupling of our three carbon homologating agent 1 with the well known Garner aldehyde 4. Further suitable and stereocontrolled functionalizations of the intermediate 9 will provide, after the base insertion, a wide class of six membered modified azanucleosides to be tested as NRTIs.

MeSH terms

  • Antiviral Agents / chemical synthesis
  • Antiviral Agents / chemistry
  • Aza Compounds / chemical synthesis
  • Aza Compounds / chemistry
  • Drug Design
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Stereoisomerism

Substances

  • Antiviral Agents
  • Aza Compounds
  • Nucleosides