Summary
Racemic ((3S,4R)-(3R,4S))-3-methyl-4-benzyloxycarbonyl-2-oxetanone has been prepared by a simple and reproductible method starting from a racemic mixture of threo-((2S,3S)-(2R,3R))-3-methylaspartic acid as chiral precursor. This α, β substituted β-lactone has been polymerized anionically, using tetraethylammonium benzoate as initiator, to yield high molecular weight and amorphous racemic threo-poly(β-benzyl-3-methylmalate). The catalytic cleavage of protecting benzyl ester groups has been conducted in different solvents and racemic threo-poly(β-3-methylmalic acid) has been obtained in N-methylpyrrolidone at room temperature. Racemic threo-poly(β-3-methylmalic acid-co-benzyl-β-3-methylmalate) has been prepared by heterogeneous H2/Pd charchoal catalyzed partial hydrogenolysis of the polymer precursor. Solubility of these different materials has been considered. Hydrolysis of threo-poly(β-3-methylmalic acid) has conducted to racemic threo-3-methylmalic acid. High resolution 13C NMR and selective INEPT NMR have been used for resonances assignment of polymers and copolymers. This new poly(β-hydroxy acid) type polyester expands the family of poly(β-malic acid) derivatives by opening the route for tailor making functional polystereoisomers with two stereogenic centers in the main chain and with the presence of an hydrophobic alkyl group and an hydrophilic carboxylic acid group in the macromolecule.
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Cammas, S., Renard, I., Girault, J.P. et al. Poly(β-3-methylmalic acid): A new degradable functional polyester with two stereogenic centers in the main chain. Polymer Bulletin 33, 149–158 (1994). https://doi.org/10.1007/BF00297349
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DOI: https://doi.org/10.1007/BF00297349