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Chemoenzymatic Synthesis of 3′-O-Acetal-Protected 2′-Deoxynucleosides as Building Blocks for Nucleic Acid Chemistry

✍ Scribed by Tatiana Rodríguez-Pérez; Susana Fernández; Saúl Martínez-Montero; Tania González-García; Yogesh S. Sanghvi; Vicente Gotor; Miguel Ferrero

Publisher
John Wiley and Sons
Year
2010
Tongue
English
Weight
217 KB
Volume
2010
Category
Article
ISSN
1434-193X

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✦ Synopsis

Abstract

We have developed a simple and convenient synthetic strategy for the preparation of tetrahydropyranyl, 4‐methoxytetrahydropyranyl, and tetrahydrofuranyl ethers of 2′‐deoxynucleosides, which are useful building blocks for nucleic acid chemistry. Enzymatic benzoylation provides an efficient alternative for protecting the 5′‐hydroxy group of the parent nucleosides in a regioselective manner. Subsequently, tetrahydropyranylation and tetrahydrofuranylation of the 2′‐deoxynucleosides at the 3′‐hydroxy group were accomplished with p‐toluensulfonic acid, MgBr~2~, or camphorsulfonic acid as catalysts. Deprotection of the 5′‐O‐benzoyl group furnished 3′‐O‐acetal‐protected 2′‐deoxynucleosides. The three‐step process is expected to enable the large‐scale synthesis of protected nucleosides.

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