Synthesis of compounds based on a dimesitylmethane scaffold and representative binding studies showing di- vs monosaccharide preference

Dimesitylmethane-based compounds 9–17, incorporating four groups capable of serving as hydrogen bonding sites, such as pyrazole, pyrimidine, imidazole, indole and aminoalkyl groups, were prepared and their ability to complex selected carbohydrates tested. The tetrasubstituted dimesitylmethane scaffold provides a cavity of a correct shape and size for disaccharide encapsulation and its aromatic units are able to participate in CH-π interactions with the sugar substrate. First binding studies confirmed the expected di- vs monosaccharide binding preference of this type of compounds and their tendency to form strong complexes with maltoside.