Deacetylation of per-acetatylated glycopyranosides: an overall pattern for acidic catalyzis

Deacetylation of per-acetatylated glycopyranosides: an overall pattern for acidic catalyzis

Bibliographic Details
Parent link:Chemical Physics Letters
Vol. 723.— 2019.— [P. 123-127]
Corporate Authors: Национальный исследовательский Томский политехнический университет Инженерная школа новых производственных технологий Научно-образовательный центр Н. М. Кижнера, Национальный исследовательский Томский политехнический университет Исследовательская школа химических и биомедицинских технологий (ИШХБМТ)
Other Authors: Nasibullin R. T. Rinat Talgatovich, Valiev R. R. Rashid Rinatovich, Fayskanova K. M. Kseniya Mikhaylovna, Stepanova E. V. Elena Vladimirovna, Cherepanov V. N. Viktor Nikolaevich, Filimonov V. D. Viktor Dmitrievich, Sundholm D. Dage
Summary:Title screen
Acetyl protecting groups are commonly used in carbohydrate chemistry. Partially acetylated arylglycosides arenot only useful building blocks in syntheses, but they are also substantial for plant metabolism. Nonselectivebase catalysis is often used for removing the acetyl groups. Even though acid-catalyzed deacetylation might bemore selective, it is seldom used in carbohydrate chemistry, because it has not been thoroughly investigated. Inthis work, we study the acid-catalyzed deacetylation ofper-acetylated phenyl glycosides experimentally andcomputationally by using density functional theory (DFT) calculations. Based on quantum modeling, we design ageneral scheme for the stepwise acid-catalyzed deacetylation of arylglycosidesper-acetates. The approach canalso be applied on gluco- and galactopyranosides. We have studied the deacetylation reaction in solvents ofdifferent polarity and found that the activation barriers of the stepwise deacetylation mechanism increase withincreasing polarity of the solvent.
Режим доступа: по договору с организацией-держателем ресурса
Published: 2019
Subjects:
электронный ресурс
труды учёных ТПУ
aryl glycosides
acid-catalyzed deacetylation
transition state modelling
activation energy calculation
моделирование
переходные состояния
энергия активации
кислотный катализ
Online Access:https://doi.org/10.1016/j.cplett.2019.03.022
Format: Electronic Book Chapter
KOHA link:https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=664288

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