Synthesis of end-functionalized (1 → 6)-2,5-anhydro-D-glucitols via anionic cyclopolymerization of 1,2:5,6-dianhydro-3,4-di-O-methyl-D-mannitol for preparing graft copolymers

End-functionalized (1→6)-2,5-anhydro-3,4-di-O-methyl-D-glucitols ( 3a–c ) were synthesized by the anionic cyclopolymerization of 1,2:5,6-dianhydro-3,4-di-O-methyl-D-mannitol ( 1 ), followed by treatment with a terminating agent such as 4-vinylbenzyl ( 2a ), oxetanyl ( 2b ), and methacryloyl group ( 2c ). The end-functionalization proceeded in a high efficiency at 73–98%. The radical copolymerization of styrene with 3a yielded a polymer ( 5a ) whose GPC trace exhibited a unimodal peak. 5a was polystyrene with (1→6)-2,5-anhydro-3,4-di-O-methyl-D -glucitol as pendant groups whose structure was confirmed by the ¹H NMR spectrum.