Scalable total synthesis of natural vanillin-derived glucoside ω-esters

Scalable total synthesis of natural vanillin-derived glucoside ω-esters

Bibliographic Details
Parent link:Carbohydrate Research
Vol. 522.— 2022.— [108683, 7 p.]
Corporate Author: Национальный исследовательский Томский политехнический университет Исследовательская школа химических и биомедицинских технологий Лаборатория "Химическая инженерия и молекулярный дизайн"
Other Authors: Avetyan (Avetian) D. L. David Ludvigovich, Shatskiy A. Andrey, Karkas M. D. Markus, Stepanova E. V. Elena Vladimirovna
Summary:Title screen
The first total synthesis of vanilloloside, calleryanin, and a series of naturally occurring ω-esters of vanilloloside was realized through direct glycosylation of vanillin-based aglycones or late-stage derivatization of vanilloloside. All aglycones and their fragments were synthesized from vanillin as the sole aromatic precursor. Subsequently, these intermediates were used to construct various vanillin-derived glucoside ω-esters using a mild acidic deacetylation as the key synthetic step, providing the final products in the total yields of 10-50% and general purity of >95%. Additionally, the first operationally simple and sustainable synthesis of litseafoloside B was realized on large scale, avoiding the use of toxic solvents and reagents, providing an attractive alternative to isolation of this and other similar compounds from plant sources.
Режим доступа: по договору с организацией-держателем ресурса
Language:English
Published: 2022
Subjects:
электронный ресурс
труды учёных ТПУ
total synthesis
natural occurring
glycosides
vanilloloside
calleryanin
esters of glycosides
plant metabolites
синтез
гликозиды
сложные эфиры
метаболиты
Online Access:https://doi.org/10.1016/j.carres.2022.108683
Format: Electronic Book Chapter
KOHA link:https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=668680

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