Indium-mediated allylation of disaccharides

Christian Denner; Manuel Gintner; Hanspeter Kählig; Tanja M Wrodnigg; Walther Schmid

doi:10.1016/j.carres.2020.108170

Indium-mediated allylation of disaccharides

Carbohydr Res. 2020 Dec:498:108170. doi: 10.1016/j.carres.2020.108170. Epub 2020 Oct 8.

Authors

Christian Denner¹, Manuel Gintner², Hanspeter Kählig², Tanja M Wrodnigg³, Walther Schmid²

Affiliations

¹ Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, A-1090, Vienna, Austria. Electronic address: christian.denner@univie.ac.at.
² Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, A-1090, Vienna, Austria.
³ Glycogroup, Institute of Chemistry and Technology for Biobased Systems, Graz University of Technology, Stremayrgasse 9, A-8010, Graz, Austria.

PMID: 33068775
DOI: 10.1016/j.carres.2020.108170

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.

Keywords: C–C bond formation; Disaccharide; Indium-mediated allylation; Ozonolysis.

MeSH terms

Alkenes / chemistry*
Catalysis
Disaccharides / chemistry*
Indium / chemistry*
Isomerism
Ozone / chemistry

Substances

Alkenes
Disaccharides
Indium
Ozone