82629-22-9

Upstream product

• 868-85-9 Dimethyl phosphite 
• 4132-86-9 N-benzyloxycarbonylalanine 
• 121-45-9 phosphorous acid trimethyl ester 
• 122313-52-4 benzyl N-(1-methoxyethyl)carbamate 
• 621-84-1 O-benzyl carbamate 
• 67-56-1 methanol 
• 65164-80-9 diphenyl 1-(phenylmethoxycarbonylamino)ethyl phosphonate 
• 124-41-4 sodium methylate 

Downstream Products

• 1346551-16-3 N-[(1-benzyloxycarbonylamino-2-methyl)methoxyphosphinyl]glycine 
• 1346551-17-4 N-[(1-benzyloxycarbonylamino-2-methyl)methoxyphosphinyl]alanine 
• 1346551-18-5 N-[(1-benzyloxycarbonylamino-2-methyl)methoxyphosphinyl]valine 
• 1346551-19-6 N-[(1-benzyloxycarbonylamino-2-methyl)methoxyphosphinyl]leucine 
• 1352492-05-7 N-[(1-benzyloxycarbonylamino-2-methyl)methoxyphosphinyl]phenylalanine 
• 1346551-15-2 methyl hydrogen 1-(benzyloxycarbonylamino)ethyl phosphonate sodium salt 
• 121843-85-4 (R)-1-(N-benzyloxycarbonylamino)ethylphosphonic acid dimethyl ester 
• 241496-50-4 (S)-1-(N-benzyloxycarbonylamino)ethylphosphonic acid dimethyl ester 
• 145240-97-7 (R)-1-aminoethylphosphonic acid dimethyl ester 
• 1356037-51-8 C₂₇H₃₀NO₇P 
• 1356037-49-4 C₂₄H₃₂NO₇P 
• 1356037-48-3 C₂₃H₃₀NO₇P 
• 1356037-47-2 C₂₁H₂₆NO₇P 
• 1356037-46-1 benzyl {[1-(benzyloxycarbonylamino)ethyl(methoxy)phosphoryl]oxy}acetate 

Relevant academic research and scientific papers

The Synthesis of α-Aminophosphonates via Enantioselective Organocatalytic Reaction of 1-(N-Acylamino)alkylphosphonium Salts with Dimethyl Phosphite

α-Aminophosphonic acids are phosphorus analogues of α-amino acids. Compounds of this type find numerous applications in medicine and crop protection due to their unique biological activities. A crucial factor in these activities is the configuration of the stereoisomers. Only a few methods of stereoselective transformation of α-amino acids into their phosphorus analogues are known so far and all of them are based on asymmetric induction, thus involving the use of a chiral substrate. In contrast, we have focused our efforts on the development of an effective method for this type of transformation using a racemic mixture of starting N-protected α-amino acids and a chiral catalyst. Herein, a simple and efficient stereoselective organocatalytic α-amidoalkylation of dimethyl phosphite by 1-(N-acylamino)alkyltriphenylphosphonium salts to enantiomerically enriched α-aminophosphonates is reported. Using 5 mol% of chiral quinine- or hydroquinine-derived quaternary ammonium salts provides final products in very good yields up to 98% and with up to 92% ee. The starting phosphonium salts were easily obtained from α-amino acid derivatives by decarboxylative methoxylation and subsequent substitution with triphenylphosphonium tetrafluoroborate. The appropriate self-disproportionation of enantiomers (SDE) test for selected α-aminophosphonate derivatives via achiral flash chromatography was performed to confirm the reliability of the enantioselectivity results that were obtained.

Penicillin G acylase-mediated kinetic resolution of racemic 1-(N-acylamino)alkylphosphonic and 1-(N-acylamino)alkylphosphinic acids and their esters

Extensive studies on the penicillin G acylase-mediated kinetic resolution of N-acylated 1-aminoalkylphosphonic and 1-aminoalkylphosphinic acids as well as their esters were carried out to recognise the relationships between the substrate structure, reacti

Comparative studies on the amidoalkylating properties of N-(1-methoxyalkyl)amides and 1-(N-acylamino)alkyltriphenylphosphonium salts in the michaelis-arbuzov-like reaction: A new one-pot transformation of N-(1-methoxyalkyl)amides into phosphonic or phosphinic analogs of N-Acyl-α-amino acids

It was demonstrated that N-(1-methoxyalkyl)amides do not react with trimethyl phosphite under neutral or basic conditions. The treatment of N-(1-methoxyalkyl)amides with trialkyl phosphites or dialkyl phosphonites, triphenylphosphonium tetrafluoroborate, and Huenig's base caused immediate formation of the corresponding 1-(N-acylamino)-alkyltriphenylphosphonium tetrafluoroborates, followed by the slow Michaelis-Arbuzov-like reaction of phosphonium salt with phosphites or phosphonites to α-(N-acylamino)- alkanephosphonic or α-(N-acylamino)alkanephosphinic acid esters, respectively. A plausible mechanism of the considered transformations, assuming an equilibrium between N-(1-alkoxyalkyl)amide, triphenylphosphonium tetrafluoroborate, 1-(N-acylamino)alkyltriphenyl-phosphonium salt, N-acylimine, and N-acyliminium salts, is discussed.

Synthesis, characterization and activity of new phosphonate dipeptides as potential inhibitors of VanX

VanX, a Zn(II)-dependent D-ala-D-ala dipeptidase, is essential for vancomycin resistance in Enterococcus faecium. The enzymatic activity of VanX was previously found to be inhibited competitively by 2-{[(1-aminoethyl) (hydroxy) phosphoryl]oxy} propanoic acid (1B). Here we report the synthesis and characterization of seven phosphonate dipeptide analogs of D-ala-D-ala with various substituent, the activity evaluation indicated that six of these phosphonate analogs inhibit VanX with IC50 of 0.48-8.21 mM. These data revealed a structure-activity relationship which is that the large substituent group on β-carbon resulted in low binding affinity of the phonphonate analog to VanX. This information will be helpful to guide the design and synthesis of the tightly-binding inhibitors for VanX.

Synthesis and activity study of phosphonamidate dipeptides as potential inhibitors of VanX

In an effort to develop inhibitors of VanX, the phosphonamidate analogs of d-Ala-d-Ala dipeptides, N-[(1-aminoethyl) hydroxyphosphinyl]-glycine (1a), -alanine (1b), -valine (1c), -leucine (1d) and -phenylalanine (1e) were synthesized, characterized and ev

Phosphonamidate and phosphothioate dipeptides as potential inhibitors of VanX

In an effort to prepare novel inhibitors of VanX, N-[(1-aminoethyl)hydroxyphosphinyl]-D-alanine 1 and S-[(aminoethyl)hydroxyphosphinyl]-thiolacetic acid 2 were synthesized and evaluated as inhibitors of VanX. Phosphonamidate 1 was shown to be a partial co

Enantioselective synthesis of α-hydroxy and α-amino phosphonates via catalytic asymmetric hydrogenation

(equation presented) Cationic rhodium catalysts of the C2 symmetric DuPHOS (1) and BPE (2) ligands have demonstrated the ability to asymmetrically hydrogenate a novel series of enol phosphonates (3) in good to excellent enantiomeric excess unde

TOWARD NEW INHIBITORS OF D-ALANINE:D-ALANINE LIGASE: THE SYNTHESIS OF 3-AMINO BUTENYLPHOSPHONIC AND AMINOPHOSPHONAMIDIC ACIDS.

The condensation of sodium salt of tetraethyl methylenediphosphonate with N-Cbz alaninal followed by the standard acidolytic removal of protecting groups provides an efficient method for the synthesis of 3-aminobutenylphosphonic acid E 3 ; N-Cbz-aminophos

AN ANALYSIS OF THE ENZYME-INHIBITOR BINDING INTERACTIONS FOR PHOSPHONIC ACID TRANSITION STATE ANALOGS OF THERMOLYSIN

Potent inhibitors of the zinc endopeptidase thermolysin are produced on replacement of the scissile peptide linkage with phosphonamidate or phosphonate ester moieties.These inhibitors have been shown to be transition state analogs, and a comparison betwee