Synthesis of end-functionalized polymers by means of living anionic polymerization. 9. Synthesis of well-defined end-functionalized polymers with one, two, three, or four monosaccharide residues

Well-defined end-functionalized polystyrenes and polyisoprenes with monosaccharide residues were synthesized by the termination reactions of the anionic living polymer of styrene or isoprene with benzyl chloride derivatives containing acetal-protected glucofuranose (1), fructopyranose (2), galactopyranose (3), and sorbofuranose (4). Furthermore, novel well-defined end-functionalized polymers with two, three, and four monosaccharide residues were successfully synthesized by reacting polystyryllithium with 1,1-bis(3'-[(1,2;5,6-di-O-isopropylidene-alpha-D-glucofuranose-O-3-yl]methyl]phenyl]ethylene (5), followed by treating with methanol, 1 (or 3), and the octyliodide containing two acetal-protected glucofuranoses (6), respectively. The end-functionalized polystyrenes with one and two glucose residues thus synthesized were found by static light scattering measurements to form reverse micelles in cyclohexane by aggregating several polymer chains.