Unit

UNIT 14.3 Synthesis of β-L-2′-Deoxythymidine (L-dT)

  1. Claire Pierra1,
  2. David Dukhan1,
  3. Gilles Gosselin1,
  4. Jean-Pierre Sommadossi2

Published Online: 1 APR 2006

DOI: 10.1002/0471142700.nc1403s24

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Pierra, C., Dukhan, D., Gosselin, G. and Sommadossi, J.-P. 2006. Synthesis of β-L-2′-Deoxythymidine (L-dT). Current Protocols in Nucleic Acid Chemistry. 24:14.3:14.3.1–14.3.9.

Author Information

  1. 1

    Université Montpellier II, Montpellier, France

  2. 2

    Idenix Pharmaceuticals, Inc., Cambridge, Massachusetts

Publication History

  1. Published Online: 1 APR 2006
  2. Published Print: MAR 2006

Abstract

The “unnatural” l-nucleoside β-l-2′-deoxythymidine (L-dT) is a potent, specific, and selective inhibitor of the replication of hepatitis B virus (HBV), which is currently in Phase III clinical trials. This unit describes, in detail, a semi-large-scale synthesis of l-dT. This convenient methodology produces l-dT in six steps starting with l-ribose and ending with a satisfactory overall yield of l-dT, and may be applied to other 2′-deoxynucleosides, incorporating different heterocyclic bases.

Keywords:

  • anti-HBV agent;
  • semi-large-scale synthesis;
  • l-dT;
  • l-nucleosides;
  • deoxygenation reaction