66609-42-5

Upstream product

• 77526-73-9 (1-Amino-2-phenylethyl)phosphonsaeure-diethylester 
• 84690-43-7 (1-Amino-2-phenyl-ethyl)-phosphonic acid dimethyl ester 
• 88081-75-8 C₃₈H₃₂NO₁₀P 
• 107072-63-9 (S)-1--2-phenylethyl phosphonic acid 
• 6324-00-1 1-amino-2-phenylethanephosphonic acid 
• 101-41-7 benzeneacetic acid methyl ester 
• 122-78-1 phenylacetaldehyde 
• 135362-56-0 1-(N-Phenylacetylamino)-2-phenylethylphosphonic acid diisopropyl ester 
• 145240-89-7 [2-Phenyl-1-((R)-4-phenyl-oxazolidin-3-yl)-ethyl]-phosphonic acid dimethyl ester 
• 100-39-0 benzyl bromide 
• 289506-28-1 diphenyl (1-(N-tert-butoxycarbonylamino)-2-phenyl)ethylphosphonate 
• 104549-56-6 {(S)-2-Phenyl-1-[(1R,4R)-1,7,7-trimethyl-bicyclo[2.2.1]hept-(2E)-ylideneamino]-ethyl}-phosphonic acid diethyl ester 

Downstream Products

• 68839-08-7 (S)-(1-Amino-2-phenylethyl)phosphonsaeure-diethylester 
• 289506-21-4 S-ethyl, 2-(2'-imidazolyl)-4-ethenylphenyl (1-(N-tert-butoxycarbonylamino)-2-phenyl)ethylphosphonate 
• 116381-45-4 C₁₆H₁₆Cl₂NO₃P 
• 116407-98-8 (4R,6R)-2-<(1S)-2-phenyl-1-ethyl>-4,6-dimethyl-1,3,2-dioxaphosphorinane-2-oxide 
• 289506-22-5 S-H-ethyl-(1-(N-t-butoxycarbonylamino)-2-phenyl)ethylphosphonate 
• 107072-63-9 (S)-1--2-phenylethyl phosphonic acid 

Relevant academic research and scientific papers

A Methylidene Group in the Phosphonic Acid Analogue of Phenylalanine Reverses the Enantiopreference of Binding to Phenylalanine Ammonia-Lyases

Aromatic amino acid ammonia-lyases and aromatic amino acid 2,3-aminomutases contain the post-translationally formed prosthetic 3,5-dihydro-4-methylidene-5H-imidazol-5-one (MIO) group. MIO enzymes catalyze the stereoselective synthesis of α- or β-amino acid enantiomers, making these chemical processes environmentally friendly and affordable. Characterization of novel inhibitors enables structural understanding of enzyme mechanism and recognizes promising herbicide candidates as well. The present study found that both enantiomers of the aminophosphonic acid analogue of the natural substrate phenylalanine and a novel derivative bearing a methylidene at the β-position inhibited phenylalanine ammonia-lyases (PAL), representing MIO enzymes. X-ray methods unambiguously determined the absolute configuration of all tested enantiomers during their synthesis. Enzyme kinetic measurements revealed the enantiomer of the methylidene-substituted substrate analogue as being a mirror image relation to the natural l-phenylalanine as the strongest inhibitor. Isothermal titration calorimetry (ITC) confirmed the binding constants and provided a detailed analysis of the thermodynamic driving forces of ligand binding. Molecular docking suggested that binding of the (R)- and (S)-enantiomers is possible by a mirror image packing. (Figure presented.).

Biocatalyzed kinetic resolution of racemic mixtures of chiral α-aminophosphonic acids

Several fungal species namely: Aspergillus niger, Aspergillus parasiticus, Penicillium funiculosum, Trigonopsis variabilis and two different strains of Fusarium oxysporum were tested toward racemic mixtures of following phosphonic acids: 1-amino-2-methylp

Asymmetric hydrogenation of α- And β-enamido phosphonates: Rhodium(I)/monodentate phosphoramidite catalyst

High efficiency and enantioselectivity have been achieved in the Rh I-catalyzed asymmetric hydrogenation of α- and β-enamido phosphonates using a monophosphoramidite as the chiral ligand (see scheme; cod=1,5-cyclooctadiene), thus affording the optically active amino phosphonates with a turnover frequency of up to 1800 h-1 and high ee values. Copyright

Double asymmetric induction as method for the synthesis of chiral organophosphorus compounds

New examples of multistereoselective syntheses of organophosphorus compounds are described.

Enantioselective ester hydrolysis catalyzed by imprinted polymers. 2

Highly cross-linked network polymers prepared by molecular imprinting catalyzed enantioselectively the hydrolysis of N-tert-butoxycarbonyl phenylalanine-p-nitrophenyl ester (BOCPheONP). The templates were designed to allow incorporation of the key catalytic elements, found in the proteolytic enzyme chymotrypsin, into the polymer active sites. Three model systems were evaluated. These were constructed from a chiral phosphonate analogue of phenylalanine (series A, C) or L-phenylalanine (series B) attached by a labile ester linkage to an imidazole-containing vinyl monomer. Free radical copolymerization of the template with methacrylic acid (MAA) and ethylene glycol dimethacrylate (EDMA) gave a highly cross-linked network polymer. The templates could be liberated from the polymers by hydrolysis, giving catalytically active sites envisaged to contain an enantioselective binding site, a site complementary to a transition state like structure (series A, C), and a hydroxyl, imidazole, and carboxylic acid group at hydrogen bond distance. As predicted, the enantiomer of BOCPheONP complementary to the configuration of the template was preferentially hydrolyzed with D-selectivity for the series A polymers (kD/kL= 1.9) and L-selectivity for the series B polymers (kL/kD = 1.2). The maximum rate enhancement, when compared with a control polymer, prepared using a benzoyl-substituted imidazole monomer as template, was 2.5, and comparing with the imidazole monomer in solution, a maximum rate enhancement of 10 was observed. The catalytic activity was higher for polymers subjected to the nucleophilic treatment. This was explained by a higher site density and flexibility of the polymer matrix caused by this treatment. In a comparison of template rebinding to polymers imprinted with a template containing either a carboxylate (planar ground state structure) or a phosphonate (tetrahedral transition state like structure) functionality, it was observed that imprinted polymers are able to discriminate between a transition state like and a ground state structure for transesterification. However the influence of transition state stabilization on the observed rate enhancements remains obscure. Only at acidic pH's was catalysis observed, whereas at basic pH's the polymers inhibit the reaction. At a later stage, the catalytic activity of the polymers for nonactivated D- and L-phenylalanine ethyl esters was investigated. A rate enhancement of up to 3 was observed when compared to the blank. Most important, however, the polymers imprinted with a D template preferentially hydrolyzed the D-ethyl ester and exhibited saturation kinetics.

Design and synthesis of phosphinic acids that triply inhibit endothelin converting enzyme, angiotensin converting enzyme and neutral endopeptidase 24.11

We have synthesized a series of phosphinic acids as inhibitors of the metalloprotease endothelin converting enzyme (ECE). Potent ECE inhibitors 4g and 4o were identified. These compounds are members of a novel class of ECE inhibitors that are also potent inhibitors of angiotensin converting enzyme and neutral endopeptidase.

Asymmetric synthesis of α-amino phosphonic acids by diastereoselective addition of trimethyl phosphite onto chiral oxazolidines

A simple and general asymmetric synthesis of α-amino phosphonic acids is described. The method involves the highly selective addition of trialkyl phosphite onto various chiral oxazolidines. Oxazaphosphorinanes thus obtained with an excellent diastereoselectivity furnish the corresponding (S)-α-substituted amino phosphonic acids in good overall yields and high ee (77→97%) after simple deprotection.

A Highly Convenient Route to Optically Pure α-Aminophosphonic Acids

Pure diastereomers, obtained simply and directly by reaction of hypophosphorous acid salts of (R)(+) or (S)(-) - N-α-methylbenzylamine with aldehydes, can be simultaneously deprotected and oxidised in one step to provide a highly convenient synthesis of α-aminophosphonic acids in high optical purity.

ASYMMETRIC SYNTHESIS OF 1-AMINOALKYLPHOSPHONIC ACIDS

Asymmetric synthesis of Phe and Tyr phosphonic analogous has been achieved by diastereoselective alkylation of chiral 1,2,3-oxazaphospholanes, the latter being readily obtained from (-) ephedrine and chloromethylphosphonic dichloride. Key words: (-)-Ephedrine; chloromethyl phosphonic dichloride; 1,3,2-oxazaphospholanes; optically active (S) and (R) 1-aminoalkylphosphonic acids.

A simple and general method for the asymmetric synthesis of α-aminophosphonic acids

A simple and general method for the asymmetric synthesis of α-aminophosphonic acids is described. A chiral phosphonate prepared in one step from R-(-)-phenylglycinol was alkylated with good diastereoselectivity using different electrophiles.