Synthesis of dinucleoside (N3'-->MeP5') methanephosphonamidates

Org Lett. 2002 May 16;4(10):1799-802. doi: 10.1021/ol0259084.

Abstract

[structure: see text] Three different approaches were used for the synthesis of dinucleoside methanephosphonamidates [3'-NH-P(O)(CH3)O-5'], starting from dichloromethylphosphine or dichloromethanephosphonate as the phosphorus-containing moiety. 5'-DMT-3'-amino-3'-deoxythymidine and N(4)-benzoyl-5'-DMT-3'-amino-2',3'-dideoxycytidine were used as the aminonucleoside precursors and the respective 3'-protected nucleosides (thymidine or N(4)-benzoyl-2'-deoxycytidine) as the 5'-hydroxyl reagents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, High Pressure Liquid
  • Chromatography, Thin Layer
  • Circular Dichroism
  • DNA / chemistry
  • DNA / drug effects*
  • Dinucleoside Phosphates / chemical synthesis*
  • Dinucleoside Phosphates / chemistry
  • Magnetic Resonance Spectroscopy
  • Organophosphorus Compounds / chemical synthesis*
  • Organophosphorus Compounds / chemistry
  • Spectrometry, Mass, Fast Atom Bombardment

Substances

  • Dinucleoside Phosphates
  • Organophosphorus Compounds
  • DNA