Efficient synthesis of 2'-deoxynucleoside 3'-C-phosphonates: reactivity of geminal hydroxyphosphonate moiety

Nucleosides Nucleotides Nucleic Acids. 2000 Jul;19(7):1159-83. doi: 10.1080/15257770008035038.

Abstract

In this report we present a novel, simple way for the synthesis of 3'-C-phosphonate derivatives of all four basic 2'-deoxynucleosides in both fully protected and deprotected forms. The reactivity of the geminal hydroxy phosphonate moiety located at the 3'-carbon atom of the nucleoside was studied with respect to the use of this type of nucleoside phosphonic acid for the preparation of short oligonucleotides, namely, dinucleoside monophosphate analogues.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • DNA / chemical synthesis*
  • Deoxyribonucleosides / chemical synthesis*
  • Deoxyribonucleosides / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Organophosphonates / chemical synthesis*
  • Organophosphonates / chemistry*
  • Spectrophotometry

Substances

  • Deoxyribonucleosides
  • Organophosphonates
  • DNA