Practical silyl protection of ribonucleosides

  • Org Lett. 2013 Sep 20;15(18):4710-3. doi: 10.1021/ol402023c.
Thomas P Blaisdell  1 ,  Sunggi Lee ,  Pinar Kasaplar ,  Xixi Sun ,  Kian L Tan
Affiliations
  • 1. Institute of Chemical Research of Catalonia , Av. Paisos Catalans 16, 43007 Tarragona, Spain, and Boston College , 2609 Beacon Street, Chestnut Hill, Massachusetts 02467-3860, United States.
PMID: 24000770 DOI: 10.1021/ol402023c
Abstract

Herein we report the site-selective silylation of the ribonucelosides. The method enables a simple and efficient procedure for accessing suitably protected monomers for automated RNA synthesis. Switching to the opposite enantiomer of the catalyst allows for the selective silylation of the 3'-hydroxyl, which could be used in the synthesis of unnatural RNA or for the analoging of ribonucelosides. Lastly, the procedure was extended to ribavirin a potent Antiviral therapeutic.

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