A tractable and efficient one-pot synthesis of 5'-Azido-5'-deoxyribonucleosides

Molecules. 2014 Feb 21;19(2):2434-44. doi: 10.3390/molecules19022434.

Abstract

Synthetic routes to 5'-azidoribonucleosides are reported for adenosine, cytidine, guanosine, and uridine, resulting in a widely applicable one-pot methodology for the synthesis of these and related compounds. The target compounds are appropriate as precursors in a variety of purposive syntheses, as the synthetic and therapeutic relevance of azido- and amino-modified nucleosides is expansive. Furthermore, in the conversion of alcohols to azides, these methods offer a tractable alternative to the Mitsunobu and other more difficult reactions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine / chemistry
  • Alcohols / chemistry
  • Azides / chemical synthesis
  • Azides / chemistry*
  • Cytidine / chemistry
  • Deoxyribonucleosides / chemical synthesis
  • Deoxyribonucleosides / chemistry*
  • Uridine / chemistry

Substances

  • Alcohols
  • Azides
  • Deoxyribonucleosides
  • Cytidine
  • Adenosine
  • Uridine