Abstract
AbstractStability of electrochemically generated glycosyl dioxalenium ions, which are reactive intermediates of electrochemical glycosylation, is influenced by protecting groups of hydroxyl groups. tert‐Butyldiphenylsilyl group at 6‐OH stabilized the intermediate and the reaction can be performed at elevated temperature. NMR measurement at low temperature confirmed accumulation of glycosyl dioxalenium ions as glycosylation intermediates and VT‐NMR measurement revealed effect of protecting groups on stability of the intermediates. Under optimized reaction conditions determined by the VT‐NMR measurement, trisaccharide with β‐1,6‐linkage of glucoside was synthesized in 46 % yield by automated electrochemical assembly.
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