Related Experiment Video
Updated: Jul 10, 2026
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Koenigs-Knorr synthesis of cycloalkyl glycosides
Zdenek Wimmer1, Lucie Pechová, David Saman
1Institute of Organic Chemistry and Biochemistry AS CR, Flemingovo namesti 2, CZ-16610, Prague 6, Czech Republic. wimmer@uochb.cas.cz
Abstract:
Cadmium carbonate was found to be a useful promoter in the Koenigs-Knorr synthesis of 2-(4-methoxybenzyl)cyclohexyl-beta-D-glycopyranosides. Using this promoter model glucoside and galactoside derivatives of cyclic (i.e., secondary) alcohols were synthesized in 50-60 % overall yields. Diastereoisomeric mixtures of products were obtained in these syntheses, which started from racemic isomers of 2-(4-methoxy-benzyl)cyclohexanol. The prepared compounds have been purified and characterized by their (1)H- and (13)C-NMR spectra, as well as by their IR and MS spectra, in order to use them as reference compounds in planned subsequent research.
Related Concept Videos
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction
Aldol Condensation with β-Diesters: Knoevenagel Condensation
Cycloaddition Reactions: Overview
Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview
Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt condensation is...

