N-glycosylation approach to glucose-functionalized diamine and its use for protection-free synthesis of polyurea bearing glucoside pendant

Abstract

A glucose-functionalized diamine was prepared and used as a new monomer for polyurea synthesis. The diamine was prepared by N-glycosylation of 1,6-hexamethylenediamine with D-glucose. Upon adding diisocyanates to the diamine, isocyanate reacted selectively with the amino groups, not with the hydroxyl groups of the glucose-derived structure, to give the corresponding polyureas. The polyureas exhibited highly hydrophilic nature due to the presence of the glucose-derived side chain. A ternary system consisting of the glucose-functionalized diamine, piperazine, and diisocyanate gave the corresponding polyureas, where content of the glucose-derived moiety was tunable by feed ratio between the diamine and piperazine. © 2012 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem, 2013