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.

Cite this paper

@article{Hamann1994AnES, title={An electrochemical synthesis of methyl alpha-isomaltoside.}, author={Christoph Hamann and H Polligkeit and P Wolf and Zygfryd Smiatacz}, journal={Carbohydrate research}, year={1994}, volume={265 1}, pages={1-7} }