Collect. Czech. Chem. Commun. 2005, 70, 2075-2085

Cleavage of the Epimines of 1,6-Anhydrohexoses with Fluoride Anion

Jiří Kroutil* and Klára Jeništová

Department of Organic and Nuclear Chemistry, Faculty of Science, Charles University, 128 43 Prague 2, Czech Republic


Aziridine ring cleavage reactions of five N-nosylepimines (2-6) having D-talo, D-galacto, D-manno, and D-allo configurations with potassium hydrogendifluoride under various reaction conditions have been performed. The cleavage regioselectively afforded diaxial isomers of vicinal amino-fluoro derivatives of 1,6-anhydro-β-D-gluco- and mannopyranose 7-11 in 51-94% yields. Removal of 2-nitrobenzenesulfonyl protecting group with benzenethiol has been attempted in the case of compound 10.

Keywords: Cleavage reactions; Fluorine; NMR spectroscopy; Aziridines; Aminosugars; Anhydrosugars; Fluorosugars; Carbohydrates.

References: 33 live references.