Indium-mediated allylation of disaccharides

Christian Denner*, Manuel Gintner, Hanspeter Kählig, Tanja M Wrodnigg, Walther Schmid

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


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.

Original languageEnglish
Article number108170
JournalCarbohydrate Research
Early online date8 Oct 2020
Publication statusPublished - Dec 2020


  • C–C bond formation
  • Disaccharide
  • Indium-mediated allylation
  • Ozonolysis

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry


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