UNIT 1.16 Palladium-Catalyzed Cross-Coupling Reactions in C6 Modifications of Purine Nucleosides
Published Online: 1 MAR 2007
Copyright © 2007 by John Wiley and Sons, Inc.
Lab Protocol Title
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.
- Published Online: 1 MAR 2007
- Published Print: MAR 2007
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.
- cross-coupling reactions;