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Transglucosidation of methyl and ethyl D-glucopyranosides by alcoholysis
Arrhenius Laboratory, Department of Organic Chemistry, Stockholm University, S-106 91 Stockholm, Sweden.
Arrhenius Laboratory, Department of Organic Chemistry, Stockholm University, S-106 91 Stockholm, Sweden.
Linköping University, The Institute of Technology. Linköping University, Department of Physics, Chemistry and Biology, Organic Chemistry .
Arrhenius Laboratory, Department of Organic Chemistry, Stockholm University, S-106 91 Stockholm, Sweden.
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2002 (English)In: Carbohydrate Research, ISSN 0008-6215, E-ISSN 1873-426X, Vol. 337, no 6, 517-521 p.Article in journal (Refereed) Published
Abstract [en]

The transglucosidations of methyl 4-O-methyl-a- and -ß-D-glucopyranoside in ethanolic camphor-10-sulfonic acid, and of ethyl 4-O-methyl-a- and -ß-D-glucopyranoside in methanolic camphor-10-sulfonic acid, have been studied. Samples were removed at intervals and the proportions of the glucosides determined by GC of their acetates. The results show that the anomer with the inverted configuration predominates in the initially formed product (˜59-70%). This indicates that all the studied reactions proceed via the same mechanism, involving exocyclic C-O cleavage and formation of a glucopyranosylium ion, but that the eliminated alcohol exerts some steric hindrance, which favors the approach of the other alcohol from the opposite side. © 2002 Published by Elsevier Science Ltd.

Place, publisher, year, edition, pages
2002. Vol. 337, no 6, 517-521 p.
Keyword [en]
Kinetics, Mechanistic studies, Transglucosylation
National Category
Engineering and Technology
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URN: urn:nbn:se:liu:diva-47063DOI: 10.1016/S0008-6215(02)00005-8OAI: oai:DiVA.org:liu-47063DiVA: diva2:267959
Available from: 2009-10-11 Created: 2009-10-11 Last updated: 2017-12-13

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Konradsson, Peter

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