Abstract
The synthesis and polymerization of 1,6-anhydro-2,4-di-O-benzyl-3-C-methyl-3-O-methyl-β-D-glucopyranose (1) followed by debenzylation of the polymer were carried out. Stereospecific homopolymerization of 1 and its copolymerization with 1,6-anhydro-2,3,4-tri-O-benzyl-β-D-glucopyranose proceeded in the presence of phosphorus pentafluoride (PF5) as an initiator in dichloromethane at −60°C. Subsequent debenzylation gave a stereoregular homopoly-saccharide 3-C-methyl-3-O-methyl-(1→6)-α-D-glucopyranan (3) and also a stereoregular copolysaccharide consisting of 3-C-methyl-3-O-methyl- and unsubstituted (1→6)-α-D-glucopyranose units. Under conditions using less initiator for a longer time, the monomer 1 afforded a stereoirregular oligomeric product consisting of mixed α- and β-configurational units.
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Kobayashi, K., Sumitomo, H. & Takahashi, M. Regioselectively Modified Stereoregular Polysaccharides XIV. Synthesis of a C-Methylated Linear Dextran 3-C-Methyl-3-O-methyl-(1→6)-α-D-glucopyranan. Polym J 21, 559–565 (1989). https://doi.org/10.1295/polymj.21.559
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DOI: https://doi.org/10.1295/polymj.21.559