Preparation of 2′-Alkylselenouridine Derivatives via a 2-(Trimethyl­silyl)ethylselenation Approach

Shota Fukuno; Masayuki Ninomiya; Mamoru Koketsu

doi:10.1055/s-0036-1588937

Synlett, Table of Contents

Synlett 2017; 28(07): 831-834
DOI: 10.1055/s-0036-1588937

letter

Preparation of 2′-Alkylselenouridine Derivatives via a 2-(Trimethylsilyl)ethylselenation Approach

Authors

Shota Fukuno

^aDepartment of Materials Science and Technology, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan Email: koketsu@gifu-u.ac.jp
Masayuki Ninomiya

^aDepartment of Materials Science and Technology, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan Email: koketsu@gifu-u.ac.jp

^bDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
Mamoru Koketsu*

^aDepartment of Materials Science and Technology, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan Email: koketsu@gifu-u.ac.jp

^bDepartment of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan

Abstract

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Abstract

2′-O-Methylation of nucleotides is well-known to increase siRNA stability against nuclease activities. Recently, selenium-containing biomolecules have been recognized as unique biological and medicinal agents for humans. In this study, 2′-alkylselenouridine derivatives were prepared through 2-(trimethylsilyl)ethylselenation at the C2′ position of 5′-DMT-2,2′-O-cyclouridine, followed by alkylation with various haloalkanes utilizing the characteristics of a Si atom. Overall, we demonstrated the versatility of a 2-(trimethylsilyl)ethylselenyl group for the synthesis of 2′-alkylselenouridines.

Key words

selenium-containing biomolecule - 2-(trimethylsilyl)ethylselenyl group - selenation - 2′-alkylselenouridine derivative - phosphoramidite monomer

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References

References and Notes
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Preparation of 2′-Alkylselenouridine Derivatives via a 2-(Trimethyl­silyl)ethylselenation Approach

Authors

Preparation of 2′-Alkylselenouridine Derivatives via a 2-(Trimethylsilyl)ethylselenation Approach