The Alkylation of Mono- and Disaccharides Via an Initialising Electrochemical Step
- 1 March 1993
- journal article
- research article
- Published by Taylor & Francis in Journal of Carbohydrate Chemistry
- Vol. 12 (2) , 173-190
- https://doi.org/10.1080/07328309308021268
Abstract
A new approach to the formation of ether derivatives of some mono- and di-saccharides by an initialising electrochemical step is described. With the exception of the nonreducing sucrose all compounds are protected at the anomeric center. In contrast to the general procedure we replaced the common bases by platinum as an electrode material with a small hydrogen overvoltage in aprotic media, such as DMF. In this way the hydroxyl groups are transformed to alcoholate anions with the generation of hydrogen. The reaction of these electrochemically generated anions with alkylating reagents such as allyl bromide, benzyl bromide and methyl iodide results in the formation of ether derivatives.Keywords
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