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

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http://hdl.handle.net/10138/328267

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Nasibullin , R T , Valiev , R R , Faiskanova , K M , Stepanova , E , Cherepanov , V N , Filimonov , V D & Sundholm , D 2019 , ' Deacetylation of per-acetatylated glycopyranosides : An overall pattern for acidic catalyzis ' , Chemical Physics Letters , vol. 723 , pp. 123-127 . https://doi.org/10.1016/j.cplett.2019.03.022

Title: Deacetylation of per-acetatylated glycopyranosides : An overall pattern for acidic catalyzis
Author: Nasibullin, R. T.; Valiev, R. R.; Faiskanova, K. M.; Stepanova, E.; Cherepanov, V. N.; Filimonov, V. D.; Sundholm, D.
Other contributor: University of Helsinki, Department of Chemistry
Date: 2019-05-16
Language: eng
Number of pages: 5
Belongs to series: Chemical Physics Letters
ISSN: 0009-2614
DOI: https://doi.org/10.1016/j.cplett.2019.03.022
URI: http://hdl.handle.net/10138/328267
Abstract: Acetyl protecting groups are commonly used in carbohydrate chemistry. Partially acetylated arylglycosides are not only useful building blocks in syntheses, but they are also substantial for plant metabolism. Nonselective base catalysis is often used for removing the acetyl groups. Even though acid-catalyzed deacetylation might be more selective, it is seldom used in carbohydrate chemistry, because it has not been thoroughly investigated. In this work, we study the acid-catalyzed deacetylation of per-acetylated phenyl glycosides experimentally and computationally by using density functional theory (DFT) calculations. Based on quantum modeling, we design a general scheme for the stepwise acid-catalyzed deacetylation of arylglycosides per-acetates. The approach can also be applied on gluco- and galactopyranosides. We have studied the deacetylation reaction in solvents of different polarity and found that the activation barriers of the stepwise deacetylation mechanism increase with increasing polarity of the solvent.
Subject: Aryl glycosides
Acid-catalyzed deacetylation
Transition state modelling
Activation energy calculation
PROTECTING GROUPS
GLYCOSIDES
ENERGY
FRAGMENTS
CONTINUUM
COMPLEX
116 Chemical sciences
114 Physical sciences
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