Cargando…

Efficient mechanochemical synthesis of regioselective persubstituted cyclodextrins

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...

Descripción completa

Detalles Bibliográficos
Autores principales: Jicsinszky, Laszlo, Caporaso, Marina, Martina, Katia, Calcio Gaudino, Emanuela, Cravotto, Giancarlo
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5238617/
https://www.ncbi.nlm.nih.gov/pubmed/28144304
http://dx.doi.org/10.3762/bjoc.12.230
Descripción
Sumario: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.