Practical silyl protection of ribonucleosides.

Org Lett

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.

Published: September 2013

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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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3857215PMC
http://dx.doi.org/10.1021/ol402023cDOI Listing

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