Work

Selective Monoreduction of 2,4 Diazido-Dideoxy Hexoses by Hydrogenation over Lindlar Catalyst

Year: 2025

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.5c02433

Authors: Leonie Wiener, Philipp J. Gritsch, Maximilian Kaiser, Nicolas Kratena, Peter Gärtner

Institution: TU Wien

Language: English

Topic: Carbohydrate Chemistry and Synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $4,500

Funder: Austrian Science Fund