Unit

UNIT 14.5 Synthesis of 2′- and 3′-C-Methylribonucleosides

  1. Leonid Beigelman1,
  2. Sergey N. Mikhailov2

Published Online: 1 MAR 2007

DOI: 10.1002/0471142700.nc1405s28

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Beigelman, L. and Mikhailov, S. N. 2007. Synthesis of 2′- and 3′-C-Methylribonucleosides. Current Protocols in Nucleic Acid Chemistry. 28:14.5:14.5.1–14.5.26.

Author Information

  1. 1

    InterMune, Brisbane, California

  2. 2

    Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russia

Publication History

  1. Published Online: 1 MAR 2007
  2. Published Print: MAR 2007

Abstract

A simple, efficient method for the synthesis of 2′- and 3′-C-methylribonucleosides starting from a common precursor is described. This synthesis achieves conversion of 1,2:5,6-di-O-isopropylidene-3-C-methyl-α-d-allofuranose into 1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl-α,β-d-ribofuranose followed by condensation with nucleic acid bases, with a final ammonolysis leading to 3′-C-methylribonucleosides. Alternatively, the same branched allofuranose converted to l,2,3-tri-O-acetyl-5-O-p-methylbenzoyl-2-C-methyl-β-d-ribofuranose, after analogous Vorbruggen condensation and ammonolysis, provides 2′-C-methylribonucleosides.

Keywords:

  • branched-chain nucleosides;
  • anti-HCV activity;
  • synthesis;
  • methylnucleosides;
  • methylribonucleosides