Nucleoside 3',5'-cyclic H-phosphonates, new useful precursors for the synthesis of nucleoside 3',5'-cyclic phosphates and their analogues

Org Lett. 2013 Aug 16;15(16):4082-5. doi: 10.1021/ol4016404. Epub 2013 Aug 1.

Abstract

Nucleoside H-phosphonates activated with a condensing agent spontaneously formed nucleoside 3',5'-cyclic H-phosphonates. The cyclization was stereoselective and produced one of the P-diastereomers in preponderance (de ca. 80%). Nucleoside 3',5'-cyclic H-phosphonates were stereochemically unstable and underwent epimerization affording the thermodynamically more stable diastereomer as a major product (de ca. 80%). They were susceptible to hydrolysis, transesterification, and oxidation and by changing oxidation protocols nucleoside 3',5'-cyclic phosphate analogues, e.g. phosphodiesters, phosphorothioate diesters, and phosphotriesters, were obtained.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cyclization
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Nucleosides / chemical synthesis*
  • Nucleosides / chemistry
  • Nucleotides / chemical synthesis*
  • Nucleotides / chemistry
  • Organophosphonates
  • Organothiophosphorus Compounds / chemistry*
  • Oxidation-Reduction

Substances

  • Nucleosides
  • Nucleotides
  • Organophosphonates
  • Organothiophosphorus Compounds