Practical silyl protection of ribonucleosides

Thomas P. Blaisdell; Sunggi Lee; Pinar Kasaplar; Xixi Sun; Kian L. Tan

doi:10.1021/ol402023c

Practical silyl protection of ribonucleosides

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

Department of Physics and Chemistry

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

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.

Original language	English
Pages (from-to)	4710-4713
Number of pages	4
Journal	Organic Letters
Volume	15
Issue number	18
DOIs	https://doi.org/10.1021/ol402023c
State	Published - 20 Sep 2013

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10.1021/ol402023c

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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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AU - Lee, Sunggi

AU - Kasaplar, Pinar

AU - Sun, Xixi

AU - Tan, Kian L.

PY - 2013/9/20

Y1 - 2013/9/20

N2 - 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.

AB - 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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Practical silyl protection of ribonucleosides

Abstract

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