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

Internet

https://doi.org/10.1021/acs.jnatprod.9b00570