Synthesis and characterization of new stereoregular AABB-type polyamides from carbohydrate-based monomers having D-manno and L-ido configurations

Polycondensation of 1,6-diamino-1,6-dideoxy-2,3,4,5-tetra-O-methyl-D-mannitol or 1,6-diamino-1,6-dideoxy-2,3,4,5-tetra-O-methyl-L-iditol with aromatic and aliphatic dicarboxylic acids has been used to prepare a series of regio- and stereoregular AABB-type polyamides. We also describe the preparation of 1,6-diamino-1,6-dideoxy-3,4-O-isopropylidene-D-mannitol and 1,6-diamino-1,6-dideoxy-2,5-di-O-methyl-3,4-O-isopropylidene-D-mannitol and their polycondensation reactions with the same dicarboxylic acids. The obtained polyamides were gummy solids that were optically active and had a pronounced affinity for water, although most of them were not soluble in this solvent. These polyamides were characterized by viscosimetry, gel-permeation chromatography, elemental analysis, and IR and NMR spectroscopies.