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Highly chemo- and regioselective phosphitylation of 2'-deoxyribonucleosides. 2003

Takeshi Wada, and Yukiko Kato, and Kazuhiko Saigo
Department of Integrated Biosciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience Bldg 702, Kashiwa, Chiba 277-8562, Japan.

We developed a novel method for the highly chemo- and regioselective phosphitylation of the 5'-hydroxy group of 2'-deoxyribonuleosides with bis(O-tert-butyl) N,N-diethylphosphoramidite. The tert-butyl groups introduced in the thymidine 5'-O-phosphite and 2'-deoxycytidine 5'-O-phosphite were simultaneously removed within 5 min by treatment with trimethylsilyl triflate in acetonitrile to give the corresponding H-phosphonate monoesters without any side reactions.

UI MeSH Term Description Entries
D003853 Deoxyribonucleosides A purine or pyrimidine base bonded to DEOXYRIBOSE.
D017905 Phosphites Inorganic salts or organic esters of phosphorous acid that contain the (3-)PO3 radical. (From Grant & Hackh's Chemical Dictionary, 5th ed) Phosphite

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