THE ALKYLATION OF MONOSACCHARIDES AND DISACCHARIDES VIA AN INITIALIZING ELECTROCHEMICAL STEP

A new approach to the formation of ether derivatives of some mono- and disaccharides 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.