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Issue 6, 2013
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Synthesis of N,N′-diglycosylated isoindigos

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Abstract

The first N,N′-diglycosylated isoindigos were prepared by P(NEt2)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.

Graphical abstract: Synthesis of N,N′-diglycosylated isoindigos

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Publication details

The article was received on 06 May 2012, accepted on 13 Dec 2012 and first published on 14 Dec 2012


Article type: Communication
DOI: 10.1039/C2OB25866H
Citation: Org. Biomol. Chem., 2013,11, 886-895

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    Synthesis of N,N′-diglycosylated isoindigos

    D. Kleeblatt, B. Siyo, M. Hein, V. O. Iaroshenko, J. Iqbal, A. Villinger and P. Langer, Org. Biomol. Chem., 2013, 11, 886
    DOI: 10.1039/C2OB25866H

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