Reaction of bromodeoxycellulose

摘要

The aim of this paper is to show that bromodeoxycellulose, whose C-6 hydroxyl groups are regioselectively and quantitatively substituted with bromine atoms, is useful for the synthesis of cellulose derivatives. The comparison of rate constants of nucleophilic halogen substitution of halogenated methyl glycosides revealed that the rates for bromodeoxysaccharides were about 1000 times higher than those of corresponding chlorodeoxysaccharides. Bromodeoxycellulose was converted effectively to S-substituted deoxymercaptocellulose derivatives by the reaction with thiols under homogeneous conditions. Deoxymercaptocellulose samples having high degrees of substitution were obtained by the reaction of bromodeoxycellulose with thiourea and consecutive alkali treatment.