Synthesis of optically active poly(L‐α‐hydroxyisovalerate) and poly(L‐α‐hydroxyisocaproate)

Abstract

Optically active poly(L-ct-hydroxyisovalerate) and poly(L-a-hydroxyisocaproate) were prepared by the ring-opening polymerization of the corresponding glycolides, and their physical properties were studied.The polymerization conditions to obtain polymers with high molecular weight and high optical purity were also examined. ZUSAMMENFASSUNG:Optisch aktives Poly(L-a-hydroxyisovalerat) und Poly(L-a-hydroxyisocaproat) wurden durch ringoffnende Polymerisation der entsprechenden Glykolide hergestellt. Es werden die Bedingungen angegeben, die zu hochmolekularen Produkten mit hoher optischer Reinheit fiihren. AuRerdem werden die physikalischen Eigenschaften dieser Polymeren mitgeteilt.

Synthesis and properties of novel diisopropyl-functionalized polyglycolide–PEG copolymers

“…Here, we presented the detailed synthesis and characterization analysis of the L-DIPG monomer, which differs from the literature. [18][19][20][21][22] All spectra for the characterizations of compound 2 and 3 can be found in the ESI † section.…”

“…There are only a few studies related to the homopolymer of diisopropyl glycolide in the literature. [18][19][20][21][22] The synthesis of the poly(diisopropyl glycolide) homopolymer was performed, and the conformational aspects were evaluated by means of optical rotatory dispersion (ORD) and circular dichroism (CD). 18,19 Also, homopolymerization of poly(diisopropyl glycolide) was examined by varying the catalyst, temperature, and time, and the optical purity of the polymers was investigated.…”

“…18,19 Also, homopolymerization of poly(diisopropyl glycolide) was examined by varying the catalyst, temperature, and time, and the optical purity of the polymers was investigated. 20,21 The polymerization kinetics and spectroscopic and thermal properties of poly(diisopropyl glycolide) were also studied. 22 In the present work, novel PEG-based diblock and triblock copolymers of poly(diisopropyl glycolide) were synthesized in order to give a thermosensitive property to these PDIPG homopolymers for applications in drug delivery systems.…”

Crystallization and Solid-State Structure of Poly(l-2-hydroxy-3-methylbutanoic acid)

“…Modification of side-chain structure in synthetic polymers is an effective way to tune their physicochemical properties. Recently, increasing attention has been given to the side-chain-substituted poly­(lactic acid)­s (substituted PLAs): poly­(2-hydroxy­butyrate), P­(2HB) [or poly­(ethyl glycolide)]; − poly­(2-hydroxy-3-methyl­butanoic acid), P­(2H3MB) [or poly­(isopropyl glycolide)]; − poly­(2-hydroxy-4-methyl­pentanoic acid), P­(2H4MP) [or poly­(isobutyl glycolide)]; ,, poly­(hexyl glycolide); poly­(cyclohexyl glycolide); polymandelide; poly­(phenyl­lactic acid), etc. − For instance, P­[( R )-2-hydroxybutyrate] with optical purity of >99% and number-average molecular weight ( M n ) of 1.5 × 10 4 was successfully synthesized, and its basic properties were investigated by Matsumoto et al Various monomers structurally related to lactide (substituted glycolides) have been synthesized to obtain substituted PLAs with high molecular weights by Baker’s group. ,,,,, They have investigated how substitution of the glycolide ring affects the glass transition temperature ( T g ) of substituted PLAs …”

“…Thus, various kinds of substituted PLAs have been synthesized. However, there have been only a few reports on substituted PLAs with both high molecular weight (>10 4 ) and high optical purity, ,− ,, and only a few of them have some crystallinity. ,,, Therefore, the possibility of substituted PLAs as crystalline polymeric materials remains unexplored. This situation is contrasted with microbial polyesters (polyhydroxy­alkanoates), which show a crystalline nature over a wide range of side-chain structure …”