Related Experiment Video
Updated: Jan 9, 2026
Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Selective Monoreduction of 2,4 Diazido-Dideoxy Hexoses by Hydrogenation over Lindlar Catalyst
Leonie Wiener1, Philipp J Gritsch1, Maximilian Kaiser1
1Institute of Applied Synthetic Chemistry, TU Wien, A-1060 Wien, Austria.
Abstract:
A novel, mild and site-selective hydrogenation of equatorial azides in diazido hexoses, achieved using Lindlar catalyst, is reported. Optimization studies on l-β-2,4-dideoxy-diazido rhamnoside revealed exclusive reduction of the equatorial azide while axially positioned azide groups remain untouched, affording the corresponding monoamino sugar in up to 87% yield. The methodology proved reliable across different diverse substitution patterns, consistently favoring equatorial over axial azide reduction while allowing for straightforward purification and scalability.
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