Synthesis of<i>O</i>,<i>O</i>-Dialkyl 1-Aminoalkanephosphonates

Kudzin, Zbigniew H.; Kotyński, Andrzej

doi:10.1055/s-1980-29311

Cited by 32 publications

(9 citation statements)

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“…Thus, the 1 H NMR spectrum of 6 showed two doublets for three protons at δ = 1.50 and 1.57 ppm respectively. Both signals exhibit a 3 J P,C of about 12 Hz, which is typical in the methyl groups of compounds possessing a iminoethylphosphonate structure . However, compound 6 decomposed upon standing, and the 1 H NMR spectrum also showed the presence of the methyl acetylphosphonate formed from the hydrolysis of the imino group.…”

Section: Resultsmentioning

confidence: 91%

An Improved Synthesis of the Antibiotic Dehydrophos

2018

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Within this work an efficient procedure for the synthesis of the vinyl phosphonate tripeptide dehydrophos is described. This procedure constitutes a significant improvement over previously described strategies, since critical transformations in the synthesis of dehydrophos were carried out in only two synthetic steps, with higher yields and under smooth conditions. Thus, the dehydrophosphoalanine residue was generated by means of the Horner–Wadsworth–Emmons reaction of formaldehyde with a peptide bearing an aminomethylbis(phosphonate) moiety, whereas deprotection of the N‐terminal position of the thus‐obtained dehydrophosphonopeptide and partial hydrolysis of the dimethyl phosphonate residue took place simultaneously. In addition, we confirmed that the chiral integrity of the leucine residue was preserved throughout these transformations.

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Section: Resultsmentioning

confidence: 91%

An Improved Synthesis of the Antibiotic Dehydrophos

2018

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“…2.1. Synthesis of Inhibitors: d/ l-Fosfalin and β-Chloro-l-alanine Derivatives Several synthetic methodologies producing fosfalin are known, including production of its enantiomerically pure forms [17][18][19][20]. Here however, synthesis of racemic fosfalin, i.e., d/l-fosfalin, was utilized due to its more economical synthesis.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Phosphonopeptide Derivatives Incorporating Single and Dual Inhibitors

Perry

Marrs

et al. 2020

Molecules

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In diagnostic microbiology, culture media are widely used for detection of pathogenic bacteria. Such media employ various ingredients to optimize detection of specific pathogens such as chromogenic enzyme substrates and selective inhibitors to reduce the presence of commensal bacteria. Despite this, it is rarely possible to inhibit the growth of all commensal bacteria, and thus pathogens can be overgrown and remain undetected. One approach to attempt to remedy this is the use of “suicide substrates” that can target specific bacterial enzymes and selectively inhibit unwanted bacterial species. With the purpose of identifying novel selective inhibitors, six novel phosphonopeptide derivatives based on d/l-fosfalin and β-chloro-l-alanine were synthesized and tested on 19 different strains of clinically relevant bacteria. Several compounds show potential as useful selective agents that could be exploited in the recovery of several bacterial pathogens including Salmonella, Pseudomonas aeruginosa, and Listeria.

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“…One of the main reasons seems to be the high moisture sensitivity of α‐iminophosphonates compared to other imine substrates, which makes crucial to remove all the water generated during the condensation. In fact, up to date, the only examples of direct condensation products with α‐phosphorylated carbonyl compounds are the stable α‐ketophosphonate derived oximes and hydrazones . In addition, the use of alkyl amines has already shown to afford amides through an initial nucleophilic attack to the acyl phosphonate followed by elimination of the phosphonate group, making these substrates ideal for acylation reactions in the absence of acid species but not for the preparation of α‐iminophosphonates.…”

Section: Synthesis Of α‐Iminophosphonatesmentioning

confidence: 99%

α‐Iminophosphonates: Useful Intermediates for Enantioselective Synthesis of α‐Aminophosphonates

et al. 2020

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A wide range of methods for the enantioselective synthesis of α‐aminophosphonic acid derivatives have been developed over the years. Although the most used methodology is the Pudovik reaction, the use of α‐iminophosphonates for the synthesis of optically active α‐aminophosphonates has emerged during the last years. The existing methods for the synthesis of α‐phosphorylated imines and their enantioselective reactions for the synthesis of enantio‐enriched α‐aminophosphonates are summarized in this review.

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Synthesis ofO,O-Dialkyl 1-Aminoalkanephosphonates

Cited by 32 publications

References 0 publications

An Improved Synthesis of the Antibiotic Dehydrophos

An Improved Synthesis of the Antibiotic Dehydrophos

Synthesis and Antimicrobial Activity of Phosphonopeptide Derivatives Incorporating Single and Dual Inhibitors

α‐Iminophosphonates: Useful Intermediates for Enantioselective Synthesis of α‐Aminophosphonates

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