A novel synthesis of antiviral nucleoside phosphoramidate and thiophosphoramidate prodrugs via nucleoside H-phosphonamidates

Nucleosides Nucleotides Nucleic Acids. 2013;32(11):617-38. doi: 10.1080/15257770.2013.838262.

Abstract

A novel and efficient method for the preparation of antiviral nucleoside 5'-H-phosphonamidates has been developed. The oxidization of the H-phosphonamidate intermediates with iodine and sulfur afforded nucleoside 5'-phosphoramidates and 5'-thiophosphoramidates in high yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / chemistry
  • Magnetic Resonance Spectroscopy
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Organothiophosphorus Compounds / chemical synthesis*
  • Organothiophosphorus Compounds / chemistry
  • Phosphoric Acids / chemical synthesis*
  • Phosphoric Acids / chemistry
  • Prodrugs / chemical synthesis*
  • Prodrugs / chemistry
  • Pyrimidine Nucleosides / chemical synthesis*
  • Pyrimidine Nucleosides / chemistry
  • Stavudine / chemical synthesis
  • Stavudine / chemistry
  • Zidovudine / chemical synthesis
  • Zidovudine / chemistry

Substances

  • Amides
  • Antiviral Agents
  • Nucleosides
  • Organothiophosphorus Compounds
  • Phosphoric Acids
  • Prodrugs
  • Pyrimidine Nucleosides
  • Zidovudine
  • phosphoramidic acid
  • Stavudine