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Nucleic Acids Symposium Series 2003 3(1):65-66; doi:10.1093/nass/3.1.65
© 2003 by Oxford University Press
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Highly chemo- and regioselective phosphitylation of 2'-deoxyribonucleosides

Takeshi Wada, Yukiko Kato and Kazuhiko Saigo

Department of Integrated Biosciences, GraduateSchool 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.


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