Unit

UNIT 1.16 Palladium-Catalyzed Cross-Coupling Reactions in C6 Modifications of Purine Nucleosides

  1. Michal Hocek,
  2. Peter Šilhár

Published Online: 1 MAR 2007

DOI: 10.1002/0471142700.nc0116s28

Current Protocols in Nucleic Acid Chemistry

Current Protocols in Nucleic Acid Chemistry

How to Cite

Hocek, M. and Šilhár, P. 2007. Palladium-Catalyzed Cross-Coupling Reactions in C6 Modifications of Purine Nucleosides. Current Protocols in Nucleic Acid Chemistry. 28:1.16:1.16.1–1.16.17.

Author Information

  1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Prague, Czech Republic

Publication History

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

Abstract

This unit describes the cross-coupling methodology for introduction of diverse C-substituents to position 6 of purine nucleosides. Protected 6-chloropurine nucleosides undergo Pd-catalyzed cross-coupling reactions with trialkylaluminium, alkylzinc halides, aryl(tributyl)stannanes, and arylboronic acids to give the corresponding 6-substituted intermediates, which can be deprotected by treatment with NaOMe. (Acetyloxy)methylzinc iodide is used for introduction of the hydroxymethyl group, which can further be transformed to fluoromethyl and difluoromethyl groups. Most of the title 6-substituted purine ribonucleosides possess cytostatic and/or anti-HCV activity.

Keywords:

  • purines;
  • nucleosides;
  • cross-coupling reactions;
  • palladium