Suzuki-Miyaura Coupling, Heck Alkenylation, and Amidation of DMTr-Protected 5-Iodo-2'-Deoxyuridine via Palladium-catalyzed Reactions

Santosh Kori; Deepali Khandagale; Yogesh S. SanghviJose L. SerranoPedro LozanoAnant R. Kapdi

首页> 外文期刊>Current Protocols in Nucleic Acid Chemistry >Suzuki-Miyaura Coupling, Heck Alkenylation, and Amidation of DMTr-Protected 5-Iodo-2'-Deoxyuridine via Palladium-catalyzed Reactions

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Suzuki-Miyaura Coupling, Heck Alkenylation, and Amidation of DMTr-Protected 5-Iodo-2'-Deoxyuridine via Palladium-catalyzed Reactions

机译：Suzuki-Miyaura Coupling, Heck Alkenylation, and Amidation of DMTr-Protected 5-Iodo-2'-Deoxyuridine via Palladium-catalyzed Reactions

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Modification of nucleosides via cross-coupling processes has been carried out extensively on unprotected halonucleosides to produce functionalized nucleosides that are often developed for incorporation into oligonucleotides or used as fluorescent probes. This approach requires protection of the 5'-OH with the 4,4'-dimethoxytrityl (DMTr) group, which is complicated and a common cause of reaction failure. Here we report a method for direct functionalization of 5'-O-DMTr-5-iodo-2'-deoxyuridine via Suzuki-Miyaura cross-coupling, Heck alkenylation, and carboamidation. This approach facilitates rapid synthesis of a variety of C5-substituted 5'-O-DMTr-2'-deoxyuridine derivatives.

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《Current Protocols in Nucleic Acid Chemistry》 |2022年第7期|e502-1-e502-16|共16页
作者
Santosh Kori; Deepali Khandagale; Yogesh S. SanghviJose L. SerranoPedro LozanoAnant R. Kapdi;
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作者单位

Institute of Chemical Technology, Matunga, Mumbai, India;

Rasayan, Inc., Encinitas, California;

Departamento de Ingeniería Química y Ambiental, Universidad Politécnica de Cartagena, European University of Technology, Cartagena, SpainDepartamento de Bioquímica y Biología Molecular B e Inmunología, Facultad de Química, Regional Campus of International Excellence, Campus Mare Nostrum, Universidad de Murcia, Murcia, Spain;

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正文语种英语
中图分类生物化学;
关键词
carboamidation; DMTr-protected nucleoside; Heck alkenylation; Ruth linker; Suzuki-Miyaura;

Suzuki-Miyaura Coupling, Heck Alkenylation, and Amidation of DMTr-Protected 5-Iodo-2'-Deoxyuridine via Palladium-catalyzed Reactions

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