Low molecular weight gelators are interesting small molecules with potential applications as advanced materials. Carbohydrate based small molecular gelators are especially useful since they can be obtained from renewable resources. We are interested in understanding the structure and gelation relationship for monosaccharide derivatives. Previously, various 4,6-benzylidene acetal protected alpha-methyl D-glucosamine derivatives have been found to be effective low molecular weight gelators. In order to study the effect of the 4,6-benzylidene acetal functional group and probe the requirement for gelation, we synthesized and analyzed a new series of analogs in which the phenyl group is replaced by a benzyl group. This can allow us to probe the effect of the aromatic group towards the self-assembling behavior and the presence of CH-pi interaction. In this presentation, the synthesis and characterization of the amide and urea derivatives of glucosamine modified with the new 4,6 acetal protecting group will be discussed.

Synthesis and analysis of a series of <i>N</i>-acetyl D-glucosamine derivatives as organogelators

249th National Meeting (2015)

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Synthesis and analysis of a series of N-acetyl D-glucosamine derivatives as organogelators