Synthesis of 4'-selenoribonucleosides

Nucleic Acids Symp Ser (Oxf). 2007:(51):139-40. doi: 10.1093/nass/nrm070.

Abstract

We report herein the synthesis and structural aspects of 4'selenouridine (11) and 4'-selenocytidine (13), novel nucleoside derivatives. 4'Selenouridine (11) was synthesized via the stereoselective seleno-Pummerer reaction between an appropriately protected selenoxide 9 and a persilylated uracil. 4'-Selenocytidine (13) was prepared from 4'selenouridine derivative 10. To the best of our knowledge, this is the first example concerning introduction of a heterocycle into the alpha- position of a seleno atom.

MeSH terms

  • Cytidine / analogs & derivatives*
  • Cytidine / chemical synthesis
  • Cytidine / chemistry
  • Organoselenium Compounds / chemical synthesis*
  • Organoselenium Compounds / chemistry
  • Ribonucleosides / chemical synthesis*
  • Ribonucleosides / chemistry
  • Uridine / analogs & derivatives*
  • Uridine / chemical synthesis
  • Uridine / chemistry

Substances

  • 4'-selenocytidine
  • 4'-selenouridine
  • Organoselenium Compounds
  • Ribonucleosides
  • Cytidine
  • Uridine