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Updated: May 15, 2026

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
Synthesis of N,N'-diglycosylated isoindigos
Dennis Kleeblatt1, Baraa Siyo, Martin Hein
1Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany.
Abstract:
The first N,N'-diglycosylated isoindigos were prepared by P(NEt(2))(3)-mediated dimerization of acetyl protected N-glycosyl-5-alkylisatins. Subsequent deacetylation yielded the corresponding deprotected N,N'-diglycosylated isoindigos. Isatine-N-glycosides containing an unsubstituted or alkyl-substituted heterocyclic moiety and β-D-manno- and β-L-rhamno configured carbohydrate substituents were successfully transformed into the corresponding isoindigos. In contrast, isatins with β-D-gluco- or β-D-xylo configured substituents failed to give the desired products.
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