Synthesis of (2′s)-2′-deoxy-2′-C-methylpurine nucleosides and their phosphoramidites
We describe the stereoselective synthesis of (2′S)-2′-deoxy-2′-C-methyladenosine (12) and (2′S)-2′-deoxy-2′-C-methylinosine (14) as well as their corresponding cyanoethyl phosphoramidites 16 and 19 from 6-0-(2,6-dichlorophenyl)inosine as starting material. The methyl group at the 2′-position was int...
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| Autores principales: | , , , |
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| Formato: | JOUR |
| Materias: | |
| Acceso en línea: | http://hdl.handle.net/20.500.12110/paper_0018019X_v85_n5_p1284_Caballero |
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| Sumario: | We describe the stereoselective synthesis of (2′S)-2′-deoxy-2′-C-methyladenosine (12) and (2′S)-2′-deoxy-2′-C-methylinosine (14) as well as their corresponding cyanoethyl phosphoramidites 16 and 19 from 6-0-(2,6-dichlorophenyl)inosine as starting material. The methyl group at the 2′-position was introduced via a Wittig reaction (→ 3, Scheme 1) followed by a stereoselective oxidation with OsO4 (→ 4, Scheme 2). The primary-alcohol moiety of 4 was tosylated (→5) and regioselectively reduced with NaBH4 (→6). Subsequent reduction of the 2′-alcohol moiety with Bu3SnH yielded stereoselectively the corresponding (2′S)-2′-deoxy-2′-C-methylnucleoside (→8a). |
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