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

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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