Abstract
Ligation of the glycosyl donor to the glycosyl acceptor through the leaving group was performed with the aim of enforcing glycoside bond formation by an intramolecular (1.x)-shift. To this end, syntheses of alkoxymethyl (2a and b), 2-alkoxyethyl (10a and b, 13a, 16a), 3-alkoxypropenyl (27a and b), and 7-alkoxy-4-oxaheptadienyl thioglucopyranoside derivatives (35a,b and d) were carried out. Their activation with thiophilic promoter systems gave the expected glucopyranosides 5a,b and d in up to high chemical yields, yet modest anomeric control. Competition experiments showed that an intermolecular reaction course is favored in these reactions, although model considerations imply that convenient intramolecular (1,3)-, (1,4)-, (1,5)-, and (1,9)-shifts, respectively, of the glycosyl donor to the acceptor are possible.
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