Synthesis of Salicaceae Acetyl Salicins Using Selective Deacetylation and Acetyl Group Migration

Synthesis of Salicaceae Acetyl Salicins Using Selective Deacetylation and Acetyl Group Migration

Bibliographic Details
Parent link:Journal of Natural Products
Vol. 83, iss. 4.— 2020.— [P. 888-893]
Corporate Authors: Национальный исследовательский Томский политехнический университет Исследовательская школа химических и биомедицинских технологий, Национальный исследовательский Томский политехнический университет Инженерная школа новых производственных технологий Научно-образовательный центр Н. М. Кижнера
Other Authors: Romanova D. A. Darjya Aleksandrovna, Avetyan (Avetian) D. L. David Ludvigovich, Belyanin M. L. Maksim L'vovich, Stepanova E. V. Elena Vladimirovna
Summary: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
Language:English
Published: 2020
Subjects:
электронный ресурс
труды учёных ТПУ
anions
carbohydrates
genetics
ethanol
mixtures
анионы
углеводы
генетика
этанол
смеси
Online Access:https://doi.org/10.1021/acs.jnatprod.9b00570
Format: Electronic Book Chapter
KOHA link:https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=662681
Description
Summary: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
DOI:10.1021/acs.jnatprod.9b00570

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