Synthesis of Salicaceae Acetyl Salicins Using Selective Deacetylation and Acetyl Group Migration; Journal of Natural Products; Vol. 83, iss. 4
| Parent link: | Journal of Natural Products Vol. 83, iss. 4.— 2020.— [P. 888-893] |
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| Körperschaften: | , |
| Weitere Verfasser: | , , , |
| Zusammenfassung: | Title screen In the present work, the synthesis of acetylated salicins, which occur naturally in many Salicaceae species, is reported. The preparation of 2-O-acetylsalicin, 2-O-acetylchlorosalicin, and 2-O-acetylethylsalicin from peracetylated bromosalicin with selective acid-catalyzed deacetylation and one-pot nucleophilic substitution of bromine as the key steps is described. The base-catalyzed O-2 > O-6 acetyl migration afforded 6-O-acetylsalicin derivatives in good yields. Thus, the first synthesis of 6-O-acetylsalicin (fragilin) using acetyl group migration is reported as well as the synthesis of 6-O-acetylchlorosalicin and 6-O-acetylethylsalicin. The NaOMe-catalyzed deacetylation of acetylated glycosides gave salicin, chlorosalicin, and ethylsalicin recently reported from Alangium chinense. Режим доступа: по договору с организацией-держателем ресурса |
| Sprache: | Englisch |
| Veröffentlicht: |
2020
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| Schlagworte: | |
| Online-Zugang: | https://doi.org/10.1021/acs.jnatprod.9b00570 |
| Format: | Elektronisch Buchkapitel |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=662681 |
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| 200 | 1 | |a Synthesis of Salicaceae Acetyl Salicins Using Selective Deacetylation and Acetyl Group Migration |f D. A. Romanova, D. L. Avetyan, M. L. Belyanin, E. V. Stepanova | |
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| 330 | |a In the present work, the synthesis of acetylated salicins, which occur naturally in many Salicaceae species, is reported. The preparation of 2-O-acetylsalicin, 2-O-acetylchlorosalicin, and 2-O-acetylethylsalicin from peracetylated bromosalicin with selective acid-catalyzed deacetylation and one-pot nucleophilic substitution of bromine as the key steps is described. The base-catalyzed O-2 > O-6 acetyl migration afforded 6-O-acetylsalicin derivatives in good yields. Thus, the first synthesis of 6-O-acetylsalicin (fragilin) using acetyl group migration is reported as well as the synthesis of 6-O-acetylchlorosalicin and 6-O-acetylethylsalicin. The NaOMe-catalyzed deacetylation of acetylated glycosides gave salicin, chlorosalicin, and ethylsalicin recently reported from Alangium chinense. | ||
| 333 | |a Режим доступа: по договору с организацией-держателем ресурса | ||
| 461 | |t Journal of Natural Products | ||
| 463 | |t Vol. 83, iss. 4 |v [P. 888-893] |d 2020 | ||
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| 701 | 1 | |a Romanova |b D. A. |g Darjya Aleksandrovna | |
| 701 | 1 | |a Avetyan (Avetian) |b D. L. |c Chemical engineer |c Engineer of Tomsk Polytechnic University |f 1995- |g David Ludvigovich |3 (RuTPU)RU\TPU\pers\46600 |9 22258 | |
| 701 | 1 | |a Belyanin |b M. L. |c organic chemist |c Associate Professor of Tomsk Polytechnic University, Candidate of chemical sciences |f 1973- |g Maksim L'vovich |3 (RuTPU)RU\TPU\pers\31268 |9 15446 | |
| 701 | 1 | |a Stepanova |b E. V. |c chemist |c Associate Professor of Tomsk Polytechnic University, Candidate of Chemical Sciences |f 1988- |g Elena Vladimirovna |3 (RuTPU)RU\TPU\pers\34245 |9 17776 | |
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