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Updated: Dec 5, 2025

Synthesis of Indoxyl-glycosides for Detection of Glycosidase Activities
Published on: May 27, 2015
Indium-mediated allylation of disaccharides
Christian Denner1, Manuel Gintner1, Hanspeter Kählig1
1Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, A-1090, Vienna, Austria.
Abstract:
The indium-mediated allylation followed by ozonolysis has been applied for the elongation of different disaccharides such as cellobiose, lactose and maltose. This reaction sequence and per-O-acetylation produced the expected mixture of α/β-pyranoid as well as α/β-furanoid isomers. The main product in all cases adopted the β-pyranose form and could be isolated and fully characterized with the help of NMR-spin simulations. Thorough investigation of the side products throughout optimization of the conditions for the ozonolysis resulted in the discovery of a novel 12 membered bridged disaccharide.
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