Deacetylation of per-acetatylated glycopyranosides: an overall pattern for acidic catalyzis
| Parent link: | Chemical Physics Letters Vol. 723.— 2019.— [P. 123-127] |
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| Kurumsal yazarlar: | , |
| Diğer Yazarlar: | , , , , , , |
| Özet: | 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 |
| Dil: | İngilizce |
| Baskı/Yayın Bilgisi: |
2019
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| Konular: | |
| Online Erişim: | https://doi.org/10.1016/j.cplett.2019.03.022 |
| Materyal Türü: | Elektronik Kitap Bölümü |
| KOHA link: | https://koha.lib.tpu.ru/cgi-bin/koha/opac-detail.pl?biblionumber=664288 |
| Özet: | 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 |
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| DOI: | 10.1016/j.cplett.2019.03.022 |