The effect of hydrogen bonding, molecular shape, dipole moments, and chain length on the mesomorphism of some D-glucose and D-glucosamine derivatives

Diverse 4-substituted-benzyl 1-O-alpha- and beta-D-glucopyranosides, 4-substituted-benzyl 2-deoxy2-trifluoroacetamido-alpha- and beta-D-glucopyranosides and 4-substituted-benzyl 2-acetamido2-deoxy-alpha- and beta-D-glucopyranosides have been synthesized. They were prepared directly by a one-step alkylation of commercially available carbohydrate starting materials. The 4-substituted-benzyl 2-deoxy-2-trifluoroacetamido-alpha- and beta-D-glucopyranosides were cleaved to yield the corresponding free amines. The influence of hydrogen bonding, terminal dipole moments, molecular shape and chain length on the thermotropic mesomorphic behaviour of these benzyl-substituted carbohydrate amphiphiles is discussed. Comparisons between the mesomorphic behaviour of the new benzyl-substituted carbohydrates and that of the related phenyl-substituted carbohydrates, as well as the non-aromatic n-alkyl D-glucosides, are made. Although the new carbohydrates do not exhibit lyotropic phase behaviour, the 4-substitutedbenzyl 2-deoxy-2-trifluoroacetamido-alpha- and beta-D-glucopyranosides have been found to gel water at very low sugar concentrations.