Practical synthesis of a potent hepatitis C virus RNA replication inhibitor

J Org Chem. 2004 Sep 17;69(19):6257-66. doi: 10.1021/jo0491096.

Abstract

A practical, efficient synthesis of 1, a hepatitis C virus RNA replication inhibitor, is described. Starting with the inexpensive diacetone glucose, the 12-step synthesis features a novel stereoselective rearrangement to prepare the key crystalline furanose diol intermediate. This is followed by a highly selective glycosidation to couple the C-2 branched furanose epoxide with deazapurine.

MeSH terms

  • Antiviral Agents / chemical synthesis*
  • Antiviral Agents / pharmacology
  • Chromatography, High Pressure Liquid
  • Hepacivirus / genetics*
  • Magnetic Resonance Spectroscopy
  • RNA, Viral / biosynthesis*

Substances

  • Antiviral Agents
  • RNA, Viral