Efficient Synthesis of a Conformationally Rigid Polymer Based on myo-Inositol Carbonate

We have successfully synthesized the polystyrene carrying a conformationally rigid myo-inositol substituent as a possible metal-chelating ligand. We are further investigating the metal binding properties of this polymer and its applicability to the practical use such as molecular imprinting. Compounds having three syn-axial hydroxyl groups on a six membered ring draw an interest due to their ability to form complexes with many cations. The steric requirements of the cyclohexane polyols to form complexes with cations are, however, rather strict and only a few such compounds with three syn-axial hydroxyls, including cis-inositol, were known. Moreover, none of these compounds is readily available, especially in large scales. Recently, synthesis of the readily available myo-inositol 4,6-carbonate with three hydroxyl groups at the axial position on a cyclohexane was reported. To our knowledge, this was the first example of the conformationally rigid cyclohexane polyols using the readily available myo-inositol