Synthesis of Molecularly Defined Poly(Hydroxyalkanoate) from Modification of Olefins
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We describe herein the syntheses of discrete Poly(Hydroxyalkanoate)s (PHAs), which have completely defined stereochemical structure and unit sequence are described. From arbitrary olefin molecules, chiral hydroxyalkanoate (HA) monomers were obtained in 7 steps. Through the selection of the olefin molecule, the side chain and length of the backbone of PHA can be varied. Especially, (S)-7-chloro-6-hydroxyheptanoate, from allylchloride, can act as a versatile handle. Molecularly defined PHAs were synthesized by the iterative linear convergence of orthogonally protected HAs. Characterization of PHAs’ molecular structure was performed using mass spectroscopy, size exclusion chromatography (SEC), and NMR spectroscopy.