Mane, Rajendra S. ; Ghosh, Sougata ; Chopade, Balu A. ; Reiser, Oliver ; Dhavale, Dilip D. (2011) Synthesis of an adenine nucleoside containing the (8'R) epimeric carbohydrate core of amipurimycin and its biological study Journal of Organic Chemistry, 76 (8). pp. 2892-2895. ISSN 0022-3263
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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo102193q
Related URL: http://dx.doi.org/10.1021/jo102193q
Abstract
The (8'R) epimeric carbohydrate core 2 of amipurimycin was synthesized from D-glucose derived allylic alcohol 3 in 11 steps and 13% overall yield. The key steps involve an acid-catalyzed acetonide ring opening of 9 with concomitant formation of an unprecedented pyranose ring skeleton to give 2,7-dioxabicyclo[3.2.1]octane 10. The α-orientation of the furan ring in 10 readily allows the stereoselective β-glycosylation and opening of the furanose ring that on removal of protecting groups affords the pyranosyl adenine nucleoside 2. The antifungal and anticancer activities of 2 were studied.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society. |
| ID Code: | 87225 |
| Deposited On: | 16 Mar 2012 06:14 |
| Last Modified: | 19 Mar 2012 11:33 |
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