Stereocontrolled synthesis of dinucleoside phosphorothioates using a fluorous tag

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• 作者：Natsuhisa Oka ; Ryosuke Murakami ; Tomoaki Kondo ; Takeshi Wada ; ^{wada@k.u-tokyo.ac.jp}
• 关键词：Stereocontrolled synthesis ; Phosphorothioate ; Fluorous ; Oxazaphospholidine
• 刊名：Journal of Fluorine Chemistry
• 出版年：2013
• 出版时间：June, 2013
• 年：2013
• 卷：150
• 期：Complete
• 页码：85-91
• 全文大小：904 K

文摘

Dinucleoside phosphorothioates were synthesized in a stereocontrolled manner (diastereoselectivity > 99:1) by using thymidine derivatives bearing a simple perfluoroalkyl tag (C₆F₁₃ or C₈F₁₇) at the 3¡ä-end and diastereopure nucleoside 3¡ä-O-oxazaphospholidine monomers. Fluorous-tagged intermediates in the synthesis were easily purified by a simple fluorous solid-phase extraction process.