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Transglucosidation of methyl and ethyl D-glucofuranosides by alcoholysis
Arrhenius Laboratory, Dept. Organ. Chem., Stockholm U., Stockholm, Sweden.
Linköping University, The Institute of Technology. Linköping University, Department of Physics, Chemistry and Biology, Organic Chemistry .
Department of Chemistry, University of Gdansk, PL-80-952, Gdansk, Poland.
2001 (English)In: Carbohydrate Research, ISSN 0008-6215, Vol. 332, no 1, 33-39 p.Article in journal (Refereed) Published
Abstract [en]

The acid catalyzed ethanolysis of methyl 5-O-methyl-a- and -ß-D-glucofuranoside and the analogous methanolysis of ethyl 5-O-methyl-a- and -ß-D-glucofuranoside have been investigated. For all four reactions, the primarily formed transglycosylation product was a single glycoside that had the opposite anomeric configuration to the starting material. This strongly indicates that a D-glucose methyl ethyl acetal is first formed and is then ring closed by a nucleophilic attack by HO-4, giving either the starting material or a transglycosylation product with the opposite anomeric configuration. Low percentages of the methyl ethyl acetals and of dimethyl acetals were also observed in the reaction product during the methanolysis reactions. © 2001 Elsevier Science Ltd.

Place, publisher, year, edition, pages
2001. Vol. 332, no 1, 33-39 p.
Keyword [en]
Kinetics, Mechanistic studies, Transglucosylation
National Category
Engineering and Technology
URN: urn:nbn:se:liu:diva-47387DOI: 10.1016/S0008-6215(01)00074-XOAI: diva2:268283
Available from: 2009-10-11 Created: 2009-10-11 Last updated: 2011-01-13

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