Synthesis of α-L-threose nucleoside phosphonates via regioselective sugar protection

J Org Chem. 2013 Jul 19;78(14):7137-44. doi: 10.1021/jo400907g. Epub 2013 Jul 3.

Abstract

A new synthesis route to α-L-threose nucleoside phosphonates via 2-O and 3-O selectively protected L-threose is developed. The key intermediates 2-O-benzoyl-L-threonolactone and 1-O-acetyl-2-O-benzoyl-3-O-t-butyldiphenylsilyl-L-threofuranose were functionalized to synthesize 2'-deoxy-2'-fluoro- and 3'-C-ethynyl L-threose 3'-O-phosphonate nucleosides. The key intermediates developed are important intermediates for the synthesis of new L-threose-based nucleoside analogues, TNA phosphoramidites, and TNA triphosphates.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Carbohydrates / chemistry*
  • Molecular Conformation
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Organophosphonates / chemical synthesis*
  • Organophosphonates / chemistry
  • Stereoisomerism
  • Tetroses / chemical synthesis*
  • Tetroses / chemistry

Substances

  • Carbohydrates
  • Nucleosides
  • Organophosphonates
  • Tetroses
  • erythrose