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Nucleic Acids Symposium Series 2001 1(1):13-14; doi:10.1093/nass/1.1.13
© 2001 by Oxford University Press
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Stereoselective synthesis of dinucleoside phosphorothioate using enantiopure 1,2-amino alcohols as chiral auxiliaries

Natsuhisa Oka, Takeshi Wada and Kazuhiko Saigo

Department of Integrated Biosciences, Graduate School of Frontier Sciences, The University of Tokyo, FSB-702, Kashiwanoha, Kashiwa 277-8562, Japan

Diastereopure nucleoside 3'-cyclic phosphoramidites were synthesized stereoselectively from enantiopure 1,2-amino alcohols. In the presence of a novel activator, these phosphoramidites underwent the condensation with 3'-O-tert-butyldimethylsilylthymidine to give the corresponding phosphite intermediates. Upon sulfurization, followed by deprotection, dithymidine phosphorothioate was obtained in good yield with good to excellent diastereoselectivity.


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