Efficient Synthesis of UDP-Furanoses via 4,5-Dicyanoimidazole(DCI)-Promoted Coupling of Furanosyl-1-Phosphates with Uridine Phosphoropiperidate

Molecules. 2019 Feb 13;24(4):655. doi: 10.3390/molecules24040655.

Abstract

A P(V)-N activation method based on nucleoside phosphoropiperidate/DCI system has been developed for improved synthesis of diverse UDP-furanoses. The reaction conditions including temperature, amount of activator, and reaction time were optimized to alleviate the degradation of UDP-furanoses to cyclic phosphates. In addition, an efficient and facile phosphoramidite route was employed for the preparation of furanosyl-1-phosphates.

Keywords: 4,5-dicyanoimidazole; NDP-sugar; P(V)-N activation; furanosyl-1-phosphate; nucleoside phosphoropiperidate.

MeSH terms

  • Arabinose / analogs & derivatives*
  • Arabinose / chemical synthesis
  • Arabinose / chemistry
  • Imidazoles / chemistry*
  • Imino Furanoses / chemical synthesis*
  • Imino Furanoses / chemistry
  • Nucleosides / chemistry
  • Phosphates / chemistry
  • Piperidines / chemistry
  • Uridine / chemistry

Substances

  • 4,5-dicyanoimidazole
  • Imidazoles
  • Imino Furanoses
  • Nucleosides
  • Phosphates
  • Piperidines
  • arabinofuranose
  • piperidine
  • Arabinose
  • Uridine