An electrochemical synthesis of methyl alpha-isomaltoside.
A novel approach has been developed for the synthesis of methyl alpha-isomaltoside (10), comprising, as the first step, electrochemical conversion of the hydroxyl groups of methyl alpha-D-glucopyranoside into the corresponding anions. The anions subsequently react with tetra-O-acetyl-alpha-D-glucopyranosyl bromide to give methyl 2',3',4',6'-tetra-O-acetyl-alpha-isomaltoside (8) as the main product, O-deacetylation of which affords 10. The glycosidation proceeds under complete stereochemical control.
Fachbereich Chemie, Carl von Ossietzky-Universität, Oldenburg, Germany.
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D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis*; D004563:Electrochemistry / Q000379:methods; D007534:Isomaltose / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D008969:Molecular Sequence Data
D004187:Disaccharides; C091668:methylisomaltoside; D007534:Isomaltose