Thioglycosides as Potential Glycosyl Donors in Electrochemical Glycosylation Reactions. Part 1: Their Preparation and Reactivity Toward Simple Alcohols

Autor:	Jean-Claude Fischer, Aurore Gref, Sabine Berteina, André Lubineau, Gilbert Balavoine
Rok vydání:	1995
Předmět:	Electrolysis Glycosylation Radical Organic Chemistry Electrochemistry Biochemistry Medicinal chemistry law.invention chemistry.chemical_compound chemistry law Organic chemistry Phenyl group Glycosyl Reactivity (chemistry) Acetonitrile
Zdroj:	Journal of Carbohydrate Chemistry. 14:1217-1236
ISSN:	1532-2327 0732-8303
DOI:	10.1080/07328309508005406
Popis:	Constant potential electrolysis of several glycosyl donors such as substituted phenyl 2,3,4,6-tetra-O-acetyl, benzoyl or benzyl-1-thio-β-D-gluco or galactopyranosides in dry acetonitrile in the presence of various primary, secondary or tertiary alcohols performed in an undivided cell, gave preferentially β-linked saccharides in moderate to good yields according to the nature of the protective groups on the sugar moiety. 2-Deoxy-2-phthalimido-1-thio-β-D-gluco derivatives gave the β-glucosides selectively in excellent yields. It was found, as expected, that substitution of the phenyl group with methoxy or methyl radicals facilitates the electrochemical glycosylation reaction by lowering the oxidation potentials of the corresponding thioglycosides.
Databáze:	OpenAIRE
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