Mane, Rajendra S. and Ghosh, Sougata and Chopade, Balu A. and Reiser, Oliver and 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,
Full text not available from this repository. (Request a copy)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 alpha-orientation of the furan ring in 10 readily allows the stereoselective beta-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 |
|---|---|
| Uncontrolled Keywords: | SUGAR MOIETY; D-GLUCOSE; ACID; DERIVATIVES; FR109615; NITRONE; |
| Subjects: | 500 Science > 540 Chemistry & allied sciences |
| Divisions: | Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser |
| Depositing User: | Dr. Gernot Deinzer |
| Date Deposited: | 22 Jun 2020 10:16 |
| Last Modified: | 22 Jun 2020 10:16 |
| URI: | https://pred.uni-regensburg.de/id/eprint/20948 |
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