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

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

• References and Notes

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