17580-61-9

Upstream product

• 104-88-1 4-chlorobenzaldehyde 
• 56-40-6 glycine 
• 5872-84-4 (2RS,3RS)-2-amino-3-(4-amino-phenyl)-3-hydroxy-propionic acid 
• 5872-74-2 (2RS,3RS)-2-amino-3-hydroxy-3-(4-nitro-phenyl)-propionic acid 

Downstream Products

• 911444-78-5 (1R,2R)-2-amino-1-(4-chlorophenyl)propane-1,3-diol 

Relevant academic research and scientific papers

PROCESS FOR PREPARING THE COMPOUND 2,2-DIFLUORO-N-((1R,2S)-3-FLUORO-1-HYDROXY-1-(4-(6-(S-METHYLSULFONIMIDOYL)PYRIDIN-3-YL)PHENYL)PROPAN-2-YL)ACETAMIDE

The present invention provides a novel process for preparing a diastereomeric mixture of the phenicol of Formula (1), its use for the treatment of bacterial infections in animals, and veterinary compositions containing the Formula (1) compound, diastereom

Synthesis method of DL-threo-p-chlorobenzene serine

The invention discloses a synthesis method of DL-threo-p-chlorobenzene serine. The synthesis method is carried out in two steps as follows: 1, reacting p-chlorobenzaldehyde with glycine under a condensation condition a to prepare a condensation intermedia

Exploring the scope of an α/β-aminomutase for the amination of cinnamate epoxides to arylserines and arylisoserines

Biocatalytic process-development continues to advance toward discovering alternative transformation reactions to synthesize fine chemicals. Here, a 5-methylidene-3,5-dihydro-4H-imidazol-4-one (MIO)-dependent phenylalanine aminomutase from Taxus canadensis (TcPAM) was repurposed to irreversibly biocatalyze an intermolecular amine transfer reaction that converted ring-substituted trans-cinnamate epoxide racemates to their corresponding arylserines. From among 12 substrates, the aminomutase ring-opened 3′-Cl-cinnamate epoxide to 3′-Cl-phenylserine 140 times faster than it opened the 4′-Cl-isomer, which was turned over slowest among all epoxides tested. GC/MS analysis of chiral auxiliary derivatives of the biocatalyzed phenylserine analogues showed that the TcPAM-transamination reaction opened the epoxides enantio- A nd diastereoselectively. Each product mixture contained (2S)+(2R)-anti (erythro) and (2S)+(2R)-syn (threo) pairs with the anti-isomers predominating (-90:10 dr). Integrating the vicinal proton signals in the 1H NMR spectrum of the enzyme-catalyzed phenylserines and calculating the chemical shift difference (?"?) between the anti and syn proton signals confirmed the diastereomeric ratios and relative stereochemistries. Application of a (2S)-threonine aldolase from E. coli further established the absolute stereochemistry of the chiral derivatives of the diastereomeric enzymatically derived products. The 2R:2S ratio for the biocatalyzed anti-isomers was highest (88:12) for 3′-NO2-phenylserine and lowest (66:34) for 4′-F-phenylserine. This showed that the stereospecificity of TcPAM is in part directed by the substituent-type on the cinnamate epoxide analogue. The catalyst also converted each cinnamate epoxide analogue to its corresponding isoserine, highlighting a biocatalytic route to arylisoserines, which play a key role in building the pharmacophore seen in anticancer and protease inhibitor drugs.

Biocatalytic Synthesis of Enantiopure β-Methoxy-β-arylalanine Derivatives

Chiral β-hydroxy-β-arylalanine and β-methoxy-β-arylalanine derivatives, which occur widely in marine nature products, were stereoselectively synthesized with 99 % ee values. The two erythro isomers were prepared by L- or D-aminoacylase-catalyzed resolution of the corresponding N-acetyl derivatives, whereas the two threo isomers were obtained only by D-aminoacylase-catalyzed resolution of the derivatives. erythro-β-Hydroxy-β-arylalanine derivatives were prepared by diastereoselective hydrogenation of ethyl 2-(hydroxyimino)-3-oxo-3-arylpropanoates, which were in turn acquired by the oximation of ethyl 3-oxo-3-arylpropanoates with ethyl nitrite in the presence of nano-K2CO3 with yields of 72 % to 80 %. β-Methoxy-β-arylalanine derivatives were synthesized through Williamson reactions between the corresponding β-hydroxy-β-arylalanines and iodomethane with silver oxide as base.

Synthesis of all stereoisomers and some congeners of isocytoxazone

cis-Isocytoxazone 2a and trans-isocytoxazone 2b, structural isomers of the antiasthmatic agent cytoxazone (-)-1, and their 5-substituted congeners 23-28 have been prepared. Aldol reaction of para-substituted benzaldehydes with 7-chloro-1-methyl-5-phenyl-1,4-benzodiazepin-2-one, followed by separation of diastereomeric racemates afforded 3-10. Acid-catalyzed 1,4-benzodiazepine ring opening, and transformation of the methyl esters of β-aryl-β-hydroxy-α-amino acids (11-16) via 4-methoxycarbonyl derivatives of 1,3-oxazolidin-2-one (17-22) and their reduction afforded the target oxazolidin-2-one derivatives 23-28. Racemic isocytoxazones 2a and 2b were prepared by an independent route starting from 4-methoxystyrene epoxide. Pure enantiomers of these diastereomeric racemates were separated by HPLC chromatography on chiral stationary phases. Their CD spectra, along with those of previously prepared enantiomers of cis-cytoxazone 1a and trans-cytoxazone 1b are discussed.