Modification of Glucose With PVC And PVA

In this study, copper catalyzed azide-alkyne cycloaddition reactions (CuAAc) known as click reactions were performed between polyvinyl chloride (PVC) and polyvinyl alcohol (PVA) with compounds that containing a terminal alkyne group.For related experiments, three different molecular weight of PVC derivatives that purchased commercial were used and PVA of 86-89% hydrolysed was used considering it?s miscibility problem in organic solvents.CuAAc are described as reactions carried out between molecules that containing terminal alkyne group and azide derivatives and yielded resulted 1,2,3-triazole derivatives. Polymer derivatives as azide containing groups and especially D-glucose, hept-1-yne and 2-propyn-1-ol as containing a terminal alkyne groups were prefered.PVC molecules of different molecular weights were converted to the azide derivatives with NaN3 by SN2 reactions. For conversion to the azide derivative of crude PVA, in the first step tosyl derivative of PVA with tosyl chloride and then related azide derivative was sythesized with NaN3 from tosylated PVA derivative.Click reactions were carried out between azide derivatives of these polymers and hept-1-yne and 2-propyn-1-ol. So, related products were synthesized that are containing 1,2,3-triazole ring.Starting from D-glucose molecule, 1,2-O-isopropylidene-?-D-glucofuranose and 1,2:5,6-di-O-isopropylidene-?-D-glucofuranose were synthesized by protecting reactions of free OH groups. Then, 1,2:5,6-di-O-isopropylidene-3-O-(2-propyn-1-yl)-?-D-glucofuranose was synthesized with NaH, and 3-bromo-prop-1-alkyn from 1,2:5,6-di-O-isopropylidene-?-D-glucofuranose molecule.For to form a terminal alkyne group of 1,2-O-isopropylidene-?-D-glucofuranose 's hydroxyl group of number 6, primary free hydroxyl group of number 6 was preserved with trimethyl acetyl chloride and after the free -OH groups of number 3 and 5 were preserved with 2,2-DMP. Then, trimethyl acetyl group was removed by alkaline hydrolysis. So, 1,2:3,5-di-O-isopropylidene-?-D-glucofuranose was synthesized. Finally, 1,2:3,5-di-O-isopropylidene-6-O-(2-prop-1-yl)-?-D-glucofuranose was synthesized that contain terminal alkyne group with NaH and 3-bromo-prop-1-alkyne.In the same ways, 1,2:3,4-di-O-isopropylidene-6-O-(2-prop-1-yl)-?-D-galactopyranose was synthesized, after the protection reactions of D-galactose?s free hydroxyl goups and then reacted with NaH and 3-bromo-prop-1-in.Click reactions were performed between synthesized molecules that are 1,2:5,6-di-O-isopropylidene-3-O-(2-prop-1-yl)-?-D-glucofuranose and 1,2:3,5-di-O-isopropylidene-6-O-(2-prop-1-yl)-?-D-glucofuranose with derivatives of PVA-N3 and PVC-N3. So, related polymer derivatives were synthesized that containing triazole ring.