This study investigates the synthesis, characterization, and biological activity of novel polymeric thia-crown ethers. On of the best solutions to save time and costs by mobilizing the chiral macrocycles on polymers which allows the recyclability and green conditions, The selecting of glucose as a model for the synthesis of macrocyclic thia crown ether The synthesis of thia-crown ether is started with protection of 4,6-positions on methyl D-glucopyranoside 1 by benzylidene protecting group, the reaction of compound 2 with bis(2-chloroethyl)ether under basic conditions to get compound 3 to obtain the structure which is ready to build up the macrocycle, the chloride can be enhanced by replacing it by iodide applying Flenksteien reaction to get compound 4. The macrocycle5 was treated in different reagent to get two derivatives in which 6 has only one free hydroxyl group, and 7 with two functional groups The compound 6 was crafted the PVC in order to obtain the target linear polymer 8. In the same context, the cross-linked polymer 9. All the compounds and polymers have been characterized by the instrumental techniques, include FT-IR, 1HNMR, 13CNMR and FESEM. The macrocycles 6, 7 and its polymeric materials was examined against two strains of bacteria, Gram + and Gram.