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Yoshito Kishi (1937-2023)

Professor. Yoshito Kishi,
a member of the Honorary Editorial Associates of HETEROCYCLES,
has passed away on January 9, 2023 at the age of 85.
I deeply express my regret over his death.
Kunio Ogasawara
Editor
January 13, 2023
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December 24, 2019
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■ 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.
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