A Simple Synthesis of 2′-Deoxy-3′-Thioinosine and Its Phosphorothioamidite

Qianfu Luo; Renjun Cheng; Qiu Wang; Shuming Bao

doi:10.1055/s-0032-1317713

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(1): 106-110
DOI: 10.1055/s-0032-1317713

paper

A Simple Synthesis of 2′-Deoxy-3′-Thioinosine and Its Phosphorothioamidite

Qianfu Luo*

Key Lab for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, P. R. of China Fax: +86(021)64250597 eMail: luoqf@ecust.edu.cn

,

Renjun Cheng

Key Lab for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, P. R. of China Fax: +86(021)64250597 eMail: luoqf@ecust.edu.cn

,

Qiu Wang

Key Lab for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, P. R. of China Fax: +86(021)64250597 eMail: luoqf@ecust.edu.cn

,

Shuming Bao

Key Lab for Advanced Materials and Institute of Fine Chemicals, East China University of Science and Technology, Shanghai 200237, P. R. of China Fax: +86(021)64250597 eMail: luoqf@ecust.edu.cn

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Abstract

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Abstract

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_N2 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.

Key words

stereoselective synthesis - heterocycles - medicinal chemistry - nucleosides

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Referenzen

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