Synthesis of C2-symmetrical polyhydroxyazepanes as inhibitors of glycosidases

Article abstract of DOI:10.1016/0960-894X(96)00183-7

Two C₂-symmetrical bis-epoxides were prepared from D-mannitol and were subjected to nucleophilic displacements with allylamine and benzylamine. Initial intermolecular epoxide opening, followed by a preferred intramolecular 7-endo-tetragol cyclization, afforded protected polyhydroxyazepanes as major products. Compound 15 was found to inhibit seven different glycosidases with K(i) in the micromolar range.