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Nucleic Acids Symposium Series 2004 48(1):57-58; doi:10.1093/nass/48.1.57
© 2004 by Oxford University Press
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Stereocontrolled synthesis of phosphorothioate RNA by the oxazaphospholidine approach

Takeshi Wada, Satoshi Fujiwara, Terutoshi Sato, Natsuhisa Oka and Kazuhiko Saigo

Department of Integrated Biosciences, Graduate School of Frontier Sciences, The University of Tokyo, Bioscience Bldg 702, Kashiwa, Chiba 277-8562, Japan

Stereoregulated diribonucleoside phosphorothioates were synthesized by the use of 2'-O-TBDMS-protected ribonucleoside 3'-O-oxazaphospholidine derivatives as monomers and N-(cyanomethyl)ammonium salts as activators. Diastereoselectivity of the condensation reaction was found to be highly dependent on the substituent groups of the oxazaphospnolidine ring as well as the structure of the activators. By the use of the optimized oxazaphospholidine monomers and activators, diastereopure diribonucleoside phosphorothioate bearing Rp and Sp configurations were obtained in good yields.


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