文献类型：期刊文献

英文题名：A Simple Synthesis of 2′-Deoxy-3′-Thioinosine and Its Phosphorothioamidite

作者：Luo, Qianfu[1];Cheng, Renjun;Wang, Qiu;Bao, Shuming

机构：[1]E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China; E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China

年份：2013

卷号：45

期号：1

起止页码：106

外文期刊名：SYNTHESIS-STUTTGART

收录：;EI(收录号：20130115857617);WOS:【SCI-EXPANDED(收录号:WOS:000313322900013)，CCR-EXPANDED(收录号:WOS:000313322900013)】；

基金：We thank the National Nature Science Foundation of China (No. 20702014) and the Fundamental Research Funds for the Central Universities of China (WK1114053) for their financial support. We are grateful to Professor H. Tian of the East China University of Science and Technology for his valuable support for this project.

语种：英文

外文关键词：stereoselective synthesis; heterocycles; medicinal chemistry; nucleosides

摘要：5'-O-{[Bis(4-methoxyphenyl)(phenyl)methyl])-2'-deoxy-3'-thioinosine and its S-phosphorothioamidite were prepared in five and six steps, respectively, from commercially available 2'-deoxyinosine. The key 3'-thio intermediate was synthesized by two sequential configuration inversions: a one-pot oxidation/reduction reaction and an S(N)2 reaction. This intermediate was readily converted into the target compound with a high yield. Compared with other methods, this synthetic strategy has the advantages of brief reaction steps, a relatively high overall yield, and regioselectivity for the configuration inversions. The products might be useful as intermediates for the preparation of new functionalized nucleosides.