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. 2013 Sep 20;15(18):4710-3.
doi: 10.1021/ol402023c. Epub 2013 Sep 3.

Practical silyl protection of ribonucleosides

Thomas P Blaisdell  1 , Sunggi Lee, Pinar Kasaplar, Xixi Sun, Kian L Tan
Affiliations

Practical silyl protection of ribonucleosides

Thomas P Blaisdell et al. Org Lett. .

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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Figures

Figure 1
Figure 1
Design of Scaffolding Catalysts
Figure 2
Figure 2
Functionalization of ribavirin
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