Fluoronucleosides, isothiocyanato C-nucleosides, and thioureylene di-C-nucleosides via cyclic sulfates

J Org Chem. 2002 Apr 19;67(8):2577-87. doi: 10.1021/jo0110303.

Abstract

Cyclic sulfates of N- and C-nucleosides (D-ribo and D-erythro configurations, respectively) are used to prepare 3'-fluoro and 3'-azido D-xylo N-nucleosides and L-threo C-nucleosides. The reduction of the 3'-azido C-nucleosides (furan, imidazoline-2-thione, and pyrrole derivatives) gives 3'-amino C-nucleosides, which, by reaction with thiocarbonyldiimidazole, are transformed into 3'-isothiocyanato C-nucleosides. Reaction of the 3'-amino with the 3'-isothiocyanato C-nucleosides gives thioureylene di-C-nucleosides, a type of nucleotide analogue with a nonionic bridge isosteric of the phosphate group.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azides / chemistry
  • Chemistry, Organic / methods
  • Chromatography, Thin Layer
  • Cyclization
  • Hydrocarbons, Fluorinated / chemistry
  • Isothiocyanates / chemistry
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Molecular Structure
  • Nucleosides* / chemical synthesis
  • Nucleosides* / chemistry
  • Spectrophotometry, Infrared
  • Spectroscopy, Fourier Transform Infrared
  • Stereoisomerism
  • Sulfates / chemistry*
  • Thionucleosides / chemistry

Substances

  • Azides
  • Hydrocarbons, Fluorinated
  • Isothiocyanates
  • Nucleosides
  • Sulfates
  • Thionucleosides