Synthesis and selective deprotection of the penta- N-protected polyamine 1,16-diamino-4,8,13-triazahexadecane

Abstract

The synthesis of the penta- N-protected polyamine thermopentamine (PA 3343, 1a, tert-butyl N-[4-benzyl-16-diallylamino-13-(pyridine-2-suilfonyl)-9-trifluoroacetyl-4,9,13-triazahexadec-1-yl]-carbamate), containing five different N-protecting groups is described. These protecting groups include tert-butoxycarbonyl, benzyl, trifluoroacetyl, diallyl, and pyridine-2-sulfonyl. In spite of the syntheses of specific polyamine derivatives the selective removal of each of these groups has been investigated.