121843-85-4

Upstream product

• 60687-34-5 (R)-<1-(N-carbobenzoxyamino)ethyl>phosphonic acid 
• 149-73-5 trimethyl orthoformate 
• 501-53-1 benzyl chloroformate 
• 145240-97-7 (R)-1-aminoethylphosphonic acid dimethyl ester 
• 868-85-9 Dimethyl phosphite 
• 147169-13-9 benzyl N-<1-((p-methylphenyl)sulfonyl)ethyl>carbamate 
• 4132-86-9 N-benzyloxycarbonylalanine 
• 186581-53-3 diazomethane 
• 71937-28-5 (1R)-(-)-1-aminoethylphosphinic acid 
• 82629-22-9 1-(N-benzyloxycarbonylamino)ethylphosphonic acid dimethyl ester 

Downstream Products

• 121843-86-5 (R)-benzyl 1-(monomethoxyphosphoryl)ethylcarbamate 

Relevant academic research and scientific papers

Synthesis of N-Acetylmuramic Acid Derivatives as Potential Inhibitors of the D-Glutamic Acid-Adding Enzyme

Compounds containing N-acetyl-D-muramic acid and (L-1-aminoethyl)phosphonic acid were designed as potential inhibitors of the D-glutamic acid-adding enzyme of the biosynthesis of bacterial peptidoglycan. 2-Acetamido-2-deoxy-3-O-(R)-2-propionyl-(L-1-amino

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

Enantioselective synthesis of H -phosphinic acids bearing natural amino acid residues

The first systematic study on the asymmetric synthesis of H-phosphinic acids bearing natural protein amino acid residues was reported on the basis of the asymmetric addition of ethyl diethoxymethylphosphinate to N-tert-butanesulfinyl imines. Good yields a

Asymmetric hydrogenation with highly active IndolPhos-Rh catalysts: Kinetics and reaction mechanism

The mechanism of the IndolPhos-Rh-catalyzed asymmetric hydrogenation of prochiral olefins has been investigated by means of X-ray crystal structure determination, kinetic measurements, high-pressure NMR spectroscopy, and DFT calculations. The mechanistic study indicates that the reaction follows an unsaturate/dihydride mechanism according to Michaelis Menten kinetics. A large value of KM (KM = 5.01 ± 0.16 M) is obtained, which indicates that the Rh-solvate complex is the catalyst resting state, which has been observed by high-pressure NMR spectroscopy. DFT calculations on the substrate-catalyst complexes, which are undetectable by experimental means, suggest that the major substrate-catalyst complex leads to the product. Such a mechanism is in accordance with previous studies on the mechanism of asymmetric hydrogenation reactions with C1-symmetric heteroditopic and monodentate ligands.

An easy entry to optically active α-amino phosphonic acid derivatives using phase-transfer catalysis (PTC)

The unprecedented use of phase-transfer catalysis (PTC) in an asymmetric hydrophosphonylation reaction allows the obtainment of a range of optically active α-amino phosphonic acid derivatives directly from α-amido sulfones. The Royal Society of Chemistry.

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