Breathing air as oxidant: Optimization of 2-chloro-2-oxo-1,3,2-dioxaphospholane synthesis as a precursor for phosphoryl choline derivatives and cyclic phosphate monomers

Becker, Greta; Wurm, Frederik R.

doi:10.1016/j.tet.2017.05.037

Cited by 14 publications

(12 citation statements)

References 30 publications

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“…We recently optimized the reaction, using CoCl 2 as catalyst and oxygen from the dried air instead of elemental oxygen, making the synthesis process more convenient and shorten the reaction time from days to hours. 313 The final monomers are obtained by esterification of COP with an appropriate alcohol (yield for esterification step 30-70%). Their purification is sometimes challenging due to the high ringstrain: column chromatography over deactivated silica or distillation at reduced pressure are typical purification methods, but sometimes reduce the yields.…”

Section: Cyclic Phosphatesmentioning

confidence: 99%

Functional biodegradable polymers via ring-opening polymerization of monomers without protective groups

2018

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Biodegradable polymers are of current interest and chemical functionality in such materials is often demanded in advanced biomedical applications. Functional groups often are not tolerated in the polymerization process of ring-opening polymerization (ROP) and therefore protective groups need to be applied. Advantageously, several orthogonally reactive functions are available, which do not demand protection during ROP. We give an insight into available, orthogonally reactive cyclic monomers and the corresponding functional synthetic and biodegradable polymers, obtained from ROP. Functionalities in the monomer are reviewed, which are tolerated by ROP without further protection and allow further post-modification of the corresponding chemically functional polymers after polymerization. Synthetic concepts to these monomers are summarized in detail, preferably using precursor molecules. Post-modification strategies for the reported functionalities are presented and selected applications highlighted.

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Section: Cyclic Phosphatesmentioning

confidence: 99%

Functional biodegradable polymers via ring-opening polymerization of monomers without protective groups

2018

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“…Benzyl alcohol (BnOH, 99%, Acros Organics, Geel, Belgium) and tert-butyl alcohol ( t BuOH, 99%, Merck, NJ, USA) were distilled over BaO and stored under argon. 2-Chloro-2-oxo-1,3,2-dioxaphospholane [45], 2-tert-butoxy-2-oxo-1,3,2-dioxaphospholane t BuOEP [23], and BHT-Mg catalyst [(BНТ)Mg(µ-OBn)(THF)] 2 [46] were prepared according to previously described methods (for details, see Section S1 in the Supporting Information).…”

Section: General Experimental Remarksmentioning

confidence: 99%

Osteogenic Differentiation of Human Adipose Tissue-Derived MSCs by Non-Toxic Calcium Poly(ethylene phosphate)s

Nifant’ev

Бухарова

Dyakonov

et al. 2019

IJMS

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P.I.) 2 A.V. Topchiev Institute of Petrochemical Synthesis RAS, 29 Leninsky Pr.,Abstract: There is a current clinical need for the development of bone void fillers and bioactive bone graft substitutes. The use of mesenchymal stem cells (MSCs) that are seeded into 3D scaffolds and induce bone generation in the event of MSCs osteogenic differentiation is highly promising. Since calcium ions and phosphates promote the osteogenic differentiation of MSCs, the use of the calcium complexes of phosphate-containing polymers is highly prospective in the development of osteogenic scaffolds. Calcium poly(ethylene phosphate)s (PEP-Ca) appear to be potentially suitable candidates primarily because of PEP's biodegradability. In a series of experiments with human adipose-tissue-derived multipotent mesenchymal stem cells (ADSCs), we demonstrated that PEP-Ca are non-toxic and give rise to osteogenesis gene marker, bone morphogenetic protein 2 (BMP-2) and mineralization of the intercellular matrix. Owing to the synthetic availability of poly(ethylene phosphoric acid) block copolymers, these results hold out the possibility for the development of promising new polymer composites for orthopaedic and maxillofacial surgery.

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“…tert -Butyl alcohol (99%, Merck, Kenilworth, NJ, USA) was distilled over BaO and stored under argon. Also, 2-Chloro-2-oxo-1,3,2-dioxaphospholane [ 67 ], t BuOEP [ 38 ] and BHT-Mg [ 37 ] were prepared according to previously described methods.…”

Section: Methodsmentioning

confidence: 99%

Antibacterial Poly(ε-CL)/Hydroxyapatite Electrospun Fibers Reinforced by Poly(ε-CL)-b-poly(ethylene phosphoric acid)

Nifant’ev

Gavrilov

Tavtorkin

et al. 2021

IJMS

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In bone surgery and orthopedics, bioresorbable materials can be helpful in bone repair and countering post-op infections. Explicit antibacterial activity, osteoinductive and osteoconductive effects are essential to achieving this objective. Nonwoven electrospun (ES) fibers are receiving the close attention of physicians as promising materials for wound dressing and tissue engineering; potentially, in high contrast with dense materials, ES mats hamper regeneration of the bone extracellular matrix to a lesser extent. The use of the compositions of inherently biodegradable polyesters (poly(ε-caprolactone) PCL, poly(lactoglycolide), etc.), calcium phosphates and antibiotics is highly prospective, but the task of forming ES fibers from such compositions is complicated by the incompatibility of the main organic and inorganic ingredients, polyesters and calcium phosphates. In the present research we report the synthesis of hydroxyapatite (HAp) nanoparticles with uniform morphology, and demonstrate high efficiency of the block copolymer of PCL and poly(ethylene phosphoric acid) (PEPA) as an efficient compatibilizer for PCL/HAp mixtures that are able to form ES fibers with improved mechanical characteristics. The materials obtained in the presence of vancomycin exhibited incremental drug release against Staphylococcus aureus (St. aureus).

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Breathing air as oxidant: Optimization of 2-chloro-2-oxo-1,3,2-dioxaphospholane synthesis as a precursor for phosphoryl choline derivatives and cyclic phosphate monomers

Cited by 14 publications

References 30 publications

Functional biodegradable polymers via ring-opening polymerization of monomers without protective groups

Functional biodegradable polymers via ring-opening polymerization of monomers without protective groups

Osteogenic Differentiation of Human Adipose Tissue-Derived MSCs by Non-Toxic Calcium Poly(ethylene phosphate)s

Antibacterial Poly(ε-CL)/Hydroxyapatite Electrospun Fibers Reinforced by Poly(ε-CL)-b-poly(ethylene phosphoric acid)

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