Unit

UNIT 14.7 Synthesis of Entecavir and Its Novel Class of Analogs

  1. Ravindra K. Rawal,
  2. Uma Sharan Singh,
  3. Srinivas Gadthula,
  4. Chung K. Chu

Published Online: 1 DEC 2011

DOI: 10.1002/0471142700.nc1407s47

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Rawal, R. K., Singh, U. S., Gadthula, S. and Chu, C. K. 2011. Synthesis of Entecavir and Its Novel Class of Analogs. Current Protocols in Nucleic Acid Chemistry. 47:14.7:14.7.1–14.7.17.

Author Information

  1. The University of Georgia College of Pharmacy, Athens, Georgia

Publication History

  1. Published Online: 1 DEC 2011
  2. Published Print: DEC 2011

Abstract

Due to the slow kinetics of viral clearance and the spontaneous genetic variability of hepatitis B virus (HBV), antiviral therapy of chronic hepatitis B remains a clinical challenge. Entecavir (S.10; a 2′-deoxy carbocyclic guanosine analog with an exo-cyclic double bond on the 5′-position; Fig. 14.7.1) has been approved in the U.S. for the therapy of chronic hepatitis B. Entecavir is synthesized from d-ribose via a key allylic alcohol (S.3) intermediate. This intermediate is also utilized to synthesize entecavir-modified carbocyclic nucleosides S.13, S.15, S.19, and S.22. Curr. Protoc. Nucleic Acid Chem. 47:14.7.1-14.7.17. © 2011 by John Wiley & Sons, Inc.

Keywords:

  • carbocyclic nucleoside;
  • entecavir;
  • Mannich reaction;
  • Hoffman elimination reaction;
  • Mitsunobu coupling