Accelerating the end-to-end production of cyclic phosphate monomers with modular flow chemistry

Morodo, Romain; Riva, Raphaël; Akker, Nynke M. S. van den; Molin, Daniël; Jérôme, Christine; Monbaliu, Jean‐Christophe M.

doi:10.1039/d2sc02891c

Cited by 9 publications

(6 citation statements)

References 58 publications

(98 reference statements)

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“…Additionally, note that the efficient continuous flow method of the end-to-end preparation of cyclic phosphate monomers with a semi-continuous modular flow platform was developed very recently by Monbaliu and coll. [ 69 ].…”

Section: Design and Synthesis Of Polyphosphodiestersmentioning

confidence: 99%

Design, Synthesis and Actual Applications of the Polymers Containing Acidic P–OH Fragments: Part 1. Polyphosphodiesters

Nifant’ev

Ivchenko

2022

IJMS

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Among natural and synthetic polymers, main-chain phosphorus-containing polyacids (PCPAs) (polyphosphodiesters), stand in a unique position at the intersection of chemistry, physics, biology and medicine. The structural similarity of polyphosphodiesters PCPAs to natural nucleic and teichoic acids, their biocompatibility, mimicking to biomolecules providing the ‘stealth effect’, high bone mineral affinity of polyphosphodiesters resulting in biomineralization at physiological conditions, and adjustable hydrolytic stability of polyphosphodiesters are the basis for various biomedical, industrial and household applications of this type of polymers. In the present review, we discuss the synthesis, properties and actual applications of polyphosphodiesters.

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Section: Design and Synthesis Of Polyphosphodiestersmentioning

confidence: 99%

Design, Synthesis and Actual Applications of the Polymers Containing Acidic P–OH Fragments: Part 1. Polyphosphodiesters

Nifant’ev

Ivchenko

2022

IJMS

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“…Finally, it should be mentioned that 1 H NMR spectra in NMR solvents containing TMS are sometimes quite unexpectedly referenced with respect to residual signals. For example, in [103], the spectrum of product 1 (Figure 2) in CDCl 3 was related to the CHCl 3 line at 7.26 ppm [49,51], although TMS was visible at δ H −0.08 ppm (Figure S5). The colors of this spectrum strongly suggest that it was analyzed with MestReNova [60].…”

Section: Reference Of Nmr Spectra Using Methods A-current Statementioning

confidence: 99%

“…The line at −0.01 ppm (instead of 0.07 ppm), which most likely comes from silicone grease [49,51], reinforces this notion. Due to some structural similarities between 1 and hexamethylphosphoramide (HMPA, 2), which induces a large high-frequency shift of the CHCl3 signal [4], it is clear that the δH values reported in [103] were underestimated by 0.08 ppm, Figure 2. A similar case appears in [104], in which "NMR spectra were recorded ….…”

Section: Reference Of Nmr Spectra Using Methods A-current Statementioning

confidence: 99%

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On the Use of Deuterated Organic Solvents without TMS to Report 1H/13C NMR Spectral Data of Organic Compounds: Current State of the Method, Its Pitfalls and Benefits, and Related Issues

Nazarski

2023

Molecules

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The quite popular, simple but imperfect method of referencing NMR spectra to residual 1H and 13C signals of TMS-free deuterated organic solvents (referred to as Method A) is critically discussed for six commonly used NMR solvents with respect to their δH and δC data that exist in the literature. Taking into account the most reliable data, it was possible to recommend ‘best’ δX values for such secondary internal standards. The position of these reference points on the δ scale strongly depends on the concentration and type of analyte under study and the solvent medium used. For some solvents, chemically induced shifts (CISs) of residual 1H lines were considered, also taking into account the formation of 1:1 molecular complexes (for CDCl3). Typical potential errors that can occur as a result of improper application of Method A are considered in detail. An overview of all found δX values adopted by users of this method revealed a discrepancy of up to 1.9 ppm in δC reported for CDCl3, most likely caused by the CIS mentioned above. The drawbacks of Method A are discussed in relation to the classical use of an internal standard (Method B), two ‘instrumental’ schemes in which Method A is often implicitly applied, that is, the default Method C using 2H lock frequencies and Method D based on Ξ values, recommended by the IUPAC but only occasionally used for 1H/13C spectra, and external referencing (Method E). Analysis of current needs and opportunities for NMR spectrometers led to the conclusion that, for the most accurate application of Method A, it is necessary to (a) use dilute solutions in a single NMR solvent and (b) to report δX data applied for the reference 1H/13C signals to the nearest 0.001/0.01 ppm to ensure the precise characterization of new synthesized or isolated organic systems, especially those with complex or unexpected structures. However, the use of TMS in Method B is strongly recommended in all such cases.

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“…In 2022, Monbaliu et al reported the continuous-flow synthesis of cyclic phosphotriesters 19 that are useful as monomers of polyphosphoesters. [29] As mentioned in the introduction section, polyphosphoesters have been used as bio-compatible and bio-degradable polymers. The ring size of the cyclic monomer is important.…”

Section: Nucleophilic Substitutions Of Pcl 3 and Pocl 3 With Alcohol ...mentioning

confidence: 99%

Continuous‐/Micro‐Flow Reactions Using Highly Electrophilic PCl₃ and POCl₃

Kitamura

Fuse

2023

ChemPlusChem

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Accelerating the end-to-end production of cyclic phosphate monomers with modular flow chemistry

Abstract: Biocompatibility, tunable degradability, broad functionalities of polyphosphoesters and their potential for biomedical applications stimulated a renewed interest from the Chemistry, Medicinal Chemistry and Polymer Sciences. Commercial applications of polyphosphoesters as...

Cited by 9 publications

References 58 publications

Design, Synthesis and Actual Applications of the Polymers Containing Acidic P–OH Fragments: Part 1. Polyphosphodiesters

Design, Synthesis and Actual Applications of the Polymers Containing Acidic P–OH Fragments: Part 1. Polyphosphodiesters

On the Use of Deuterated Organic Solvents without TMS to Report 1H/13C NMR Spectral Data of Organic Compounds: Current State of the Method, Its Pitfalls and Benefits, and Related Issues

Continuous‐/Micro‐Flow Reactions Using Highly Electrophilic PCl₃ and POCl₃

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Accelerating the end-to-end production of cyclic phosphate monomers with modular flow chemistry

Abstract: Biocompatibility, tunable degradability, broad functionalities of polyphosphoesters and their potential for biomedical applications stimulated a renewed interest from the Chemistry, Medicinal Chemistry and Polymer Sciences. Commercial applications of polyphosphoesters as...

Cited by 9 publications

References 58 publications

Design, Synthesis and Actual Applications of the Polymers Containing Acidic P–OH Fragments: Part 1. Polyphosphodiesters

Design, Synthesis and Actual Applications of the Polymers Containing Acidic P–OH Fragments: Part 1. Polyphosphodiesters

On the Use of Deuterated Organic Solvents without TMS to Report 1H/13C NMR Spectral Data of Organic Compounds: Current State of the Method, Its Pitfalls and Benefits, and Related Issues

Continuous‐/Micro‐Flow Reactions Using Highly Electrophilic PCl3 and POCl3

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Continuous‐/Micro‐Flow Reactions Using Highly Electrophilic PCl₃ and POCl₃