Indium-mediated allylation of disaccharides

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. [Display omitted] •Elongation of disaccharides.•Indium-mediated allylation of carbohydrates.•DAISY spin simulation of carbohydrates.•12 Membered bridged bicyclic carbohydrate.