title: Synthesis of N,N'-diglycosylated isoindigos.
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.
authors.affiliation: Institut für Chemie, Universität Rostock, Albert-Einstein-Str. 3a, 18059 Rostock, Germany.
authors.forename: Dennis
authors.initials: D
authors.lastname: Kleeblatt
authors.forename: Baraa
authors.initials: B
authors.lastname: Siyo
authors.forename: Martin
authors.initials: M
authors.lastname: Hein
authors.forename: Viktor O
authors.initials: VO
authors.lastname: Iaroshenko
authors.forename: Jamshed
authors.initials: J
authors.lastname: Iqbal
authors.forename: Alexander
authors.initials: A
authors.lastname: Villinger
authors.forename: Peter
authors.initials: P
authors.lastname: Langer
mesh_terms: D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006031:Glycosylation; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure
chemical_list: D006027:Glycosides; D007211:Indoles; C049010:isoindigotin