The First Total Syntheses of the Diglycosides Virgaureoside A, of Solidago virgaurea L., and its Analogue iso-Virgaureoside A

The First Total Syntheses of the Diglycosides Virgaureoside A, of Solidago virgaurea L., and its Analogue iso-Virgaureoside A

Detalhes bibliográficos
Parent link:Current Organic Synthesis.— , 2004-
Vol. 14, iss. 3.— 2017.— [P. 394-397]
Autor Corporativo: Национальный исследовательский Томский политехнический университет (ТПУ) Институт физики высоких технологий (ИФВТ) Кафедра биотехнологии и органической химии (БИОХ)
Outros Autores: Stepanova E. V. Elena Vladimirovna, Nagornaya M. O. Marina Olegovna, Belyanin M. L. Maksim L'vovich, Filimonov V. D. Viktor Dmitrievich
Resumo:Title screen
Background: Virgaureoside A is a component of Solidago virgaurea L. (Goldenrod ordinary) which is a well-known remedy in folk Chinese medicine. However, the isolation and, consequently, pharmacological testing of this diglycoside is difficult due to its low content.Objective: To perform the first total synthesis of the diglycoside Virgaureoside A and apply the developed synthetic approach to the synthesis of analogues compound, iso-Virgareoside A, thus allowing the acquisition of these diglycosides in any desired quantity and thereby permit an assessment of their potential biological properties.Results: The first syntheses of Virgaureoside A [2-(?-D-glucopyranosyloxy)benzyl 2-(?-D-glucopyranosyloxy) benzoate], a diglycoside of the Solidago virgaurea L. plant, and iso-Virgaureoside A [2-(?-D-glucopyranosyloxy) benzyl 4-(?-D-glucopyranosyloxy)benzoate], which is not found in nature and has not been described in the literature, have been accomplished. The key step involved selective acid catalyzed cleavage of acetyl esters in the presence of a substituted benzoyl ester and two glycosidic linkages.Conclusion: The desired products Virgaureoside A and iso-Virgaureoside A were synthesized in four steps in 5.6% and 3.0% overall yield, starting from ethyl 2-hydroxybenzoate and ethyl 4-hydroxybenzoate, respectively.
Режим доступа: по договору с организацией-держателем ресурса
Idioma:inglês
Publicado em: 2017
Assuntos:
электронный ресурс
труды учёных ТПУ
дигликозиды
фармакологическое действие
синтез
Acesso em linha:http://dx.doi.org/10.2174/1570179413666161031144533
Formato: Recurso Eletrônico Capítulo de Livro
KOHA link:https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=654933

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