Transglucosidation of methyl and ethyl D-glucofuranosides by alcoholysis
2001 (English)In: Carbohydrate Research, ISSN 0008-6215, Vol. 332, no 1, 33-39 p.Article in journal (Refereed) Published
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.
Kinetics, Mechanistic studies, Transglucosylation
Engineering and Technology
IdentifiersURN: urn:nbn:se:liu:diva-47387DOI: 10.1016/S0008-6215(01)00074-XOAI: oai:DiVA.org:liu-47387DiVA: diva2:268283