Synthesis and O-phosphorylation of 3,3,4,4-tetrafluoroaryl-C-nucleoside analogues

Org Biomol Chem. 2010 Mar 21;8(6):1445-54. doi: 10.1039/b922442d. Epub 2010 Jan 25.

Abstract

Enantioenriched tetrafluorinated aryl-C-nucleosides were synthesised in four steps from 1-benzyloxy-4-bromo-3,3,4,4-tetrafluorobutan-2-ol. The presence of the tetrafluorinated ethylene group is compatible with O-phosphorylation of the primary alcohol, as demonstrated by the successful preparation of the tetrafluorinated naphthyl-C-nucleotide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Butanols / chemistry
  • Halogenation
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry*
  • Oxygen / chemistry*
  • Phosphorylation
  • Stereoisomerism
  • Substrate Specificity

Substances

  • Butanols
  • Nucleosides
  • Oxygen