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Synthesis of (2′S)-2′-Deoxy-2′-C-methylpurine Nucleosides and Their Phosphoramidites

✍ Scribed by Gerardo Caballero; Mariana Gallo; Javier M. Montserrat; Adolfo M. Iribarren

Publisher
John Wiley and Sons
Year
2002
Tongue
German
Weight
154 KB
Volume
85
Category
Article
ISSN
0018-019X

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✦ Synopsis

We describe the stereoselective synthesis of (2'S)-2'-deoxy-2'-C-methyladenosine ( ) and (2'S)-2'-deoxy-2'-C-methylinosine ( ) as well as their corresponding cyanoethyl phosphoramidites 16 and 19 from 6-O-(2,6dichlorophenyl)inosine as starting material. The methyl group at the 2'-position was introduced via a Wittig reaction ( 3 3, Scheme 1) followed by a stereoselective oxidation with OsO 4 ( 3 4, Scheme 2). The primaryalcohol moiety of 4 was tosylated ( 3 5) and regioselectively reduced with NaBH 4 ( 3 6). Subsequent reduction of the 2'-alcohol moiety with Bu 3 SnH yielded stereoselectively the corresponding (2'S)-2'-deoxy-2'-Cmethylnucleoside ( 3 8a).

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