<i>D</i>_3<i>h</i>-Symmetrical Hydrogen-Bonding Unit as a Saccharide Recognition and Self-Assembling Module

A D3h-symmetrical triresorcinol module 1,3,5-tris(2,6-dihydroxy-4-pentylphenyl)benzene (3) was investigated in terms of its hydrogen-bonding ability for glycoside recognition and self-association. When 3 was treated with glycoside, corresponding changes were induced in 1H NMR, UV, and CD spectra. The titration experiments indicated the participation of not only a 1:1 but also a 1:2 association of a glucosamine derivative guest. Self-association of 3 caused gelation with CDCl3, and was studied by 1H NMR and X-ray analysis.