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Updated: May 15, 2025

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
Gold-Catalyzed Intramolecular Coupling Reduction for Direct Synthesis of Indole-Fused Iminosugars
Lijing Feng1, Likai Zhou1,2, Weilin Yang1
1Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Material Science, Hebei University, Baoding, Hebei 071002, P. R. China.
Abstract:
In the presence of Hantzsch ester and with JohnPhosAuCl/AgOMs as catalysts, a series of indole-fused iminosugars were obtained in good yields by the intramolecular reductive coupling reaction of iminosugar C-glycoside, in which the terminal alkyne could be coupled with indole and further reduced to methyl. The substrates of iminosugar C-glycosides were conveniently prepared by a three-component reaction of tosylated/mesylated sugar, propargylamine, and indole derivatives. The advantages of this protocol are its simplicity and efficiency in constructing the complex indole-fused iminosugars.
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