SYNTHESIS OF (THIO)UREIDO-LINKED AMINOPOLYOL-DERIVED AMPHIPHILES AND BOLAAMPHIPHILES

摘要

Molecular aggregation and self-assembly represent the underlying features of soft matter as exemplified by gels and liquid crystals, which are attractive domains of applied science. Recently, we have reported the systematic preparation of a novel family of carbohydrate amphiphiles and bolaamphiphiles, in which hydrophilic and hydrophobic units are connected through ureido or bis-ureido linkages. The sugar unit comes from aminopolyols such as D-glucamine (1) and N-methyl-D-glucamine (2). We describe herein the synthesis of new amphipathic structures combining a polar carbohydrate moiety from aminopoliols 1-4 and a lipophylic fragment of heterocumulenes 5-8, through one or more urea or thiourea groups which are otherwise non-ionic isosteric replacements of the phosphate linkage.