36097-39-9

Upstream product

• 105962-57-0 (Z)-methyl 2-acetamido-3-(4-nitrophenyl)acrylate 
• 17193-40-7 (S)-4-nitrophenylalanine methyl ester hydrochloride 
• 75-36-5 acetyl chloride 
• 3618-96-0 (S)-N-acetylphenylalanine 
• 63-91-2 L-phenylalanine 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 66693-69-4 2-amino-3-(4-nitrophenyl)propionic acid hydrochloride 
• 17193-40-7 (+)-Methyl 2-amino-3-(4-nitrophenyl)propionate hydrochloride 
• 109-21-7 butyl butyrate 
• 127090-51-1 2-acetylamino-3-(4-nitro-phenyl)-propionic acid methyl ester 
• 20877-15-0 ethyl 2-acetylamino-2-cyano-3-(4-nitrophenyl)propanoate 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 555-16-8 4-nitrobenzaldehdye 
• 66949-13-1 (Z)-2-methyl-4-(4-nitrobenzylidene)oxazol-5(4H)-one 

Downstream Products

• 36097-42-4 2(S)-acetylamino-3-(4-amino-phenyl)-propionic acid methyl ester 
• 60521-91-7 Ac-Phe(4-NHAc)-OMe 
• 864238-42-6 D,L-4-Acetamido-N-acetyl-3-nitrophenylalanine methyl ester 
• 864238-27-7 Fmoc-Phe(4-NH₂-3-NO₂)-OH 
• 76311-21-2 ester methylique de la N-acetyl-p-(methacrylamido acetamido) L-phenylalanine 
• 792864-20-1 N-phthalimido-4-(bis-2-chloroethyl)amino-L-phenylalanine ethyl ester 
• 97338-02-8 N-phthalimido-4-(bis-2-hydroxyethyl)amino-L-phenylalanine ethyl ester 
• 74743-23-0 N-phthalimido-4-amino-L-phenylalanine ethyl ester 
• 17451-67-1 N-phthalimido-4-nitro-L-phenylalanine ethyl ester 
• 34276-53-4 ethyl (S)-2-amino-3-(4-nitrophenyl)propionate 
• 147065-06-3 L-nitrophenylalanine hydrochloride 

Relevant academic research and scientific papers

Mechanistically Guided One Pot Synthesis of Phosphine-Phosphite and Its Implication in Asymmetric Hydrogenation

Although hybrid bidentate ligands are known to yield highly enantioselective products in asymmetric hydrogenation (AH), synthesis of these ligands is an arduous process. Herein, a one pot, atom-economic synthesis of a hybrid phosphine-phosphite (L1) is reported. After understanding the reactivity difference between an O-nucleophile versus C-nucleophile, one pot synthesis of Senphos (L1) was achieved (72 %). When L1 was treated with [Rh], 31P NMR revealed bidentate coordination to Rh. Senphos, in the presence of rhodium, catalyzes the AH of Methyl-2-acetamido-3-phenylacrylate and discloses an unprecedented turn over frequency of 2289, along with excellent enantio-selectivity (92 %). The generality is demonstrated by hydrogenating an array of alkenes. The AH operates under mild conditions of 1–2 bar H2 pressure, at room temperature. The practical relevance of L1 is demonstrated by scaling-up the reaction to 1 g and by synthesizing DOPA, a drug widely employed for the treatment of Parkinson's disease. Computational insights indicate that the R isomer is preferred by 3.8 kcal/mol over the S isomer.

Diaza-Crown Ether-Bridged Chiral Diphosphoramidite Ligands: Synthesis and Applications in Asymmetric Catalysis

A small library of diaza-crown ether-bridged chiral diphosphoramidite ligands was prepared. In the rhodium-catalyzed asymmetric hydrogenation and hydroformylation reactions, these ligands exhibited distinct properties in catalytic activity and/or enantioselectivity. Hydrogenated products with opposite absolute configurations could be obtained in high yields with excellent ee values by utilizing (S,S)-L1 and (S,S)-L3, respectively. Meanwhile, the addition of alkali metal cations caused variations in catalytic outcomes, showing the supramolecular tunability of these Rh/diphosphoramidite catalytic systems.

Melphalan intermediate and preparation method thereof

The invention discloses a Melphalan intermediate and a preparation method thereof. The Melphalan intermediate is prepared by acidifying a compound p-nitrobenzaldehyde under the action of methanol, a hydrochloric acid solvent, etc. The preparation method has a route with mild reaction conditions, is higher than an existing preparation method in yield, is economical and effective, and is suitable for large-scale industrial production. The synthesis route is as shown in the description.

Temperature-controlled bidirectional enantioselectivity in a dynamic catalyst for asymmetric hydrogenation

Asymmetric catalysis using enantiomerically pure catalysts is one of the most widely used methods for the preparation of enantiomerically pure compounds. The separate synthesis of both enantiomerically pure compounds requires tedious and time-consuming pr

Asymmetric chemoenzymatic synthesis of N-acetyl-α-amino esters based on lipase-catalyzed kinetic resolutions through interesterification reactions

Several phenylalanine analogs have been synthesized through a four-step route starting from easily available ethyl acetamidocyanoacetate. In a first reaction, and making use of phase transfer catalysts, this compound reacted with several alkyl halides, being benzyltributylammonium chloride identified as the best one for the production of a series of quaternary amino acids in moderate to excellent yields (52-95%). Then, the corresponding N-acetyl-phenylalanine methyl and allyl ester derivatives were obtained through acidic hydrolysis, esterification, and N-acetylation. Rhizomucor miehei lipase was found as a versatile enzyme for the resolution of these amino esters, finding the best results through interesterification reactions with butyl butyrate in acetonitrile. A great influence in the stereoselectivity was found depending on the chemical structure of the compound, achieving for the non- or para-substituted in the phenyl ring excellent stereoselectivities, being moderate for the meta-nitro derivative, while the ortho-nitro amino ester did not react.

Synthesis and study of 2-acetyl amino-3-[4-(2-amino-5-sulfo-phenylazo)- phenyl]-propionic acid: A new class of inhibitor for hen egg white lysozyme amyloidogenesis

The compounds capable of blocking the aggregation of amyloidogenic proteins may have therapeutic potentials. We report on the synthesis of 2-acetyl amino-3-[4-(2-amino-5-sulfo-phenylazo)-phenyl]-propionic acid as an HEWL (hen egg white lysozyme) amyloid inhibitor starting from phenylalanine. The compounds arrest the monomers and exhibit anti-aggregating activity. Moreover, the acetyl derivative 1 served as a better inhibitor than the trifluoroacetyl derivative 2 against in vitro amyloid fibrillogenesis of the HEWL model system.

Damage of aromatic amino acids by the atmospheric free radical oxidant NO3 in the presence of NO2, N2O4, O3 and O2

Analysis of the products formed in the reaction of NO3 with the N- and C-protected aromatic amino acids 1-5, which was performed under conditions that simulate exposure of biosurfaces to environmental pollutants, revealed insight how this impor

Enantioselective hydrogenation of α-dehydroamino acid esters catalyzed by rhodium complexes with chiral bisaminophosphine ligands

A highly efficient strategy for the synthesis of a series of chiral bisaminophosphine ligands was well established with several remarkable features. The synthetic utility of these ligands was explored for rhodium-catalyzed asymmetric hydrogenations of α-d

Supramolecular chiral phosphorous ligands based on a [2]pseudorotaxane complex for asymmetric hydrogenation

A new type of supramolecular chiral phosphorus-based ligands was prepared from easily available monodentate ligands through complexation between dibenzylammonium salt and dibenzo[24]crown-8 macrocycle. Rhodium complexes with these supramolecular ligands w

Rational design of MOFs constructed from modified aromatic amino acids

Three Phe and Tyr derivatives, 2-amino-3-(4-aminophenyl)-propionic acid (AAP), 3E-[5-(2-amino-2-carboxyethyl)-2-methoxyphenyl]-acrylic acid (AMPA) and 3-(4-aminophenyl)-2-(carboxymethyl-amino)-propionic acid (ACP) have been chosen as the ligands to constr