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Paper | Regular issue | Vol 92, No. 1, 2016, pp.64-74
Published online, 8th December, 2015
DOI: 10.3987/COM-15-13349
■ An Efficient Synthesis of 2-Selenouridine and Its Phosphoramidite Precursor

Masakazu Kogami, Darrell R. Davis, and Mamoru Koketsu*

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

Abstract

We describe an efficient and scalable synthetic route to the natural occurring 2-selenouridine (Se2U) and its suitably protected derivative for phosphoramidite synthesis. From known fully TBDMS-protected thiouridine, the corresponding selenouridine was synthesized via the reaction of methylthiouridine with NaHSe, which was then completely deprotected without affecting the selenocarbonyl moiety to deliver Se2U. Next, Se2U was converted into the 2′-O-TBDMS-5′-O-DMT derivative in 81% yield over four steps including di-tert-butylsilylene (DTBS) introduction at O3′ and O5′, O2′-silylation, selective cleavage of DTBS, and DMT introduction. This synthetic route enabled gram-scale preparation of both Se2U and its phosphoramidite precursor in excellent yields. Furthermore, the predicted C3′-endo conformational preference of Se2U was experimentally confirmed by NMR spectroscopy.