title: Efficient mechanochemical synthesis of regioselective persubstituted cyclodextrins.
abstract: A number of per-6-substituted cyclodextrin derivative syntheses have been effectively carried out in a planetary ball mill under solvent-free conditions. The preparation of Bridion®and important per-6-amino/thiocyclodextrin intermediates without polar aprotic solvents, a source of byproducts and persistent impurities, could be performed. Isolation and purification processes could also be simplified. Considerably lower alkylthiol/halide ratio were necessary to reach the complete reaction in comparison with thiourea or azide reactions. While the presented mechanochemical syntheses were carried out on the millimolar scale, they are easily scalable.
authors.affiliation: Department of Drug Science and Technology and NIS - Centre for Nanostructured Interfaces and Surfaces, University of Turin, Via P. Giuria 9, 10125 Turin (Italy).
authors.forename: Laszlo
authors.initials: L
authors.lastname: Jicsinszky
authors.affiliation: Department of Drug Science and Technology and NIS - Centre for Nanostructured Interfaces and Surfaces, University of Turin, Via P. Giuria 9, 10125 Turin (Italy).
authors.forename: Marina
authors.initials: M
authors.lastname: Caporaso
authors.affiliation: Department of Drug Science and Technology and NIS - Centre for Nanostructured Interfaces and Surfaces, University of Turin, Via P. Giuria 9, 10125 Turin (Italy).
authors.forename: Katia
authors.initials: K
authors.lastname: Martina
authors.affiliation: Department of Drug Science and Technology and NIS - Centre for Nanostructured Interfaces and Surfaces, University of Turin, Via P. Giuria 9, 10125 Turin (Italy).
authors.forename: Emanuela
authors.initials: E
authors.lastname: Calcio Gaudino
authors.affiliation: Department of Drug Science and Technology and NIS - Centre for Nanostructured Interfaces and Surfaces, University of Turin, Via P. Giuria 9, 10125 Turin (Italy).
authors.forename: Giancarlo
authors.initials: G
authors.lastname: Cravotto
keywords: green chemistry; nucleophilic substitution; planetary ball mill; siRNA delivery intermediate; sugammadex