Issue 6, 2013

Synthesis of N,N′-diglycosylated isoindigos

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

Supplementary files

Article information

Article type
Communication
Submitted
06 May 2012
Accepted
13 Dec 2012
First published
14 Dec 2012

Org. Biomol. Chem., 2013,11, 886-895

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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