Practical silyl protection of ribonucleosides
Thomas P Blaisdell1, Sunggi Lee, Pinar Kasaplar
1Institute 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.
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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