Selective deprotection of the Cbz amine protecting group for the facile synthesis of kanamycin A dimers linked at N-3″ position

The optimal conditions for the regioselective deprotection of per-N-Cbz-kanamycin A and the reaction mechanism was investigated. We found that the Cbz group at N-3″ position was selectively deprotected under milder basic conditions and the cyclic carbamate is an intermediate of the deprotection reaction. The selective deprotection of the amine protecting group enable us to synthesize several kanamycin A dimers linked at N-3″ position in a straightforward way.