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Chemoenzymatic Synthesis of 3′‐ O ‐Acetal‐Protected 2′‐Deoxynucleosides as Building Blocks for Nucleic Acid Chemistry
Author(s) -
RodríguezPérez Tatiana,
Fernández Susana,
MartínezMontero Saúl,
GonzálezGarcía Tania,
Sanghvi Yogesh S.,
Gotor Vicente,
Ferrero Miguel
Publication year - 2010
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200901428
Subject(s) - chemistry , acetal , nucleic acid , regioselectivity , combinatorial chemistry , organic chemistry , catalysis , stereochemistry , biochemistry
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.