UNIT 14.5 Synthesis of 2′- and 3′-C-Methylribonucleosides
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
Beigelman, L. and Mikhailov, S. N. 2007. Synthesis of 2′- and 3′-C-Methylribonucleosides. Current Protocols in Nucleic Acid Chemistry. 28:14.5:14.5.1–14.5.26.
- Published Online: 1 MAR 2007
- Published Print: MAR 2007
A simple, efficient method for the synthesis of 2′- and 3′-C-methylribonucleosides starting from a common precursor is described. This synthesis achieves conversion of 1,2:5,6-di-O-isopropylidene-3-C-methyl-α-d-allofuranose into 1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl-α,β-d-ribofuranose followed by condensation with nucleic acid bases, with a final ammonolysis leading to 3′-C-methylribonucleosides. Alternatively, the same branched allofuranose converted to l,2,3-tri-O-acetyl-5-O-p-methylbenzoyl-2-C-methyl-β-d-ribofuranose, after analogous Vorbruggen condensation and ammonolysis, provides 2′-C-methylribonucleosides.
- branched-chain nucleosides;
- anti-HCV activity;