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Synlett 2017; 28(07): 831-834
DOI: 10.1055/s-0036-1588937
letter
© Georg Thieme Verlag Stuttgart · New York

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

Shota Fukuno
a   Department 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
a   Department of Materials Science and Technology, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan   Email: koketsu@gifu-u.ac.jp
b   Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
,
Mamoru Koketsu*
a   Department of Materials Science and Technology, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan   Email: koketsu@gifu-u.ac.jp
b   Department of Chemistry and Biomolecular Science, Faculty of Engineering, Gifu University, 1-1 Yanagido, Gifu 501-1193, Japan
› Author Affiliations
Further Information

Publication History

Received: 22 November 2016

Accepted after revision: 22 December 2016

Publication Date:
17 January 2017 (online)

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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

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588937.
  • Supporting Information
 

  • References and Notes

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