86022-41-5

Basic information

• Product Name: Methyl threo-beta-hydroxy-4-nitro-3-phenyl-L-alaninate
• Synonyms: (2S,3R)-2-Amino-3-hydroxy-3-(4-nitro-phenyl)-propionsaeure-methylester;L-Threo-β-p-nitrophenylserinmethylester
• CAS NO: 86022-41-5
• Molecular Formula: C10H12N2O5
• Molecular Weight: 240.216
• Mol File: 86022-41-5.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Methyl threo-beta-hydroxy-4-nitro-3-phenyl-L-alaninate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl threo-beta-hydroxy-4-nitro-3-phenyl-L-alaninate(86022-41-5)
• EPA Substance Registry System: Methyl threo-beta-hydroxy-4-nitro-3-phenyl-L-alaninate(86022-41-5)

Safety Data

• Hazardous Substances Data: 86022-41-5(Hazardous Substances Data)

Upstream product

• 101570-41-6 (2RS,3RS)-3-hydroxy-2-(4-nitro-benzylidenamino)-3-(4-nitro-phenyl)-propionic acid methyl ester 
• 77809-03-1 (2RS,3SR)-3-acetoxy-2-acetylamino-3-phenyl-propionic acid methyl ester 
• 5872-74-2 (2RS,3SR)-2-amino-3-hydroxy-3-(4-nitro-phenyl)-propionic acid 
• 15917-27-8 (+/-)-methyl (βR)-β-hydroxy-4-nitro-1-phenylalaninate 
• 113299-51-7 (2RS,3SR)-2-amino-3-hydroxy-3-(4-nitro-phenyl)-propionic acid methyl ester; hydrochloride 
• 67-56-1 methanol 
• 7664-93-9 sulfuric acid 
• 118537-24-9 Methyl(2R,3S)-2-amino-3-hydroxy-3-(4-nitrophenyl)propanoate 
• 7647-01-0 hydrogenchloride 
• 1424360-99-5 (1S,2R,5S,8R,1'R)-5-(1'-hydroxy-p-nitrobenzyl)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0^2,7]undec-6-en-4-one 
• 555-16-8 4-nitrobenzaldehdye 
• 129446-45-3 (2S,3R)-2-amino-3-hydroxy-3-(4-aminophenyl)propanoic acid 

Downstream Products

• 118537-24-9 Methyl(2R,3S)-2-amino-3-hydroxy-3-(4-nitrophenyl)propanoate 
• 129446-45-3 (2S,3R)-2-amino-3-hydroxy-3-(4-aminophenyl)propanoic acid 
• 99860-60-3 (2S,3R)-2-(2,2-dichloro-acetylamino)-3-hydroxy-3-(4-nitro-phenyl)-propionic acid hydrazide 
• 101570-41-6 (2S,3R)-3-hydroxy-2-(4-nitro-benzylidenamino)-3-(4-nitro-phenyl)-propionic acid methyl ester 
• 56-75-7 chloramphenicol 
• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 122675-07-4 (2S,3R)-threo-N-acetyl-p-nitrophenylserine 
• 19185-86-5 methyl (2R,3S)-threo-N-acetyl-p-nitrophenylserinate 
• 123410-36-6 Methyl (+)-threo-N-dichloroacetyl-β-(4-nitrophenyl)serinate 
• 134-90-7 L-threo-chloramphenicol 
• 19185-86-5 methyl (+/-)-threo-N-acetyl-p-nitrophenylserinate 
• 123410-34-4 chloramphenicol 
• 123410-35-5 (-)-(2R,3S)-N-(Dichloroacetyl)-3-(4-nitrophenyl)serine methyl ester 
• 100122-47-2 Methyl (+/-)-threo-N-dichloroacetyl-β-(4-nitrophenyl)serinate 

Relevant articles and documents

ENGINEERED POLYPEPTIDES AND THEIR APPLICATIONS IN SYNTHESIS OF BETA-HYDROXY-ALPHA-AMINO ACIDS

Provided are engineered polypeptides that are useful for the asymmetric synthesis of β-hydroxy-α-amino acids under industrial-relevant conditions. The engineered polypeptides disclosed are developed through directed evolution based on the ability of catalytic synthesis of (2S, 3R) -2-amino-3-hydroxy-3- (4-nitrophenyl) propanoic acid. Also provided are polynucleotides encoding the engineered polypeptides, host cells capable of expressing engineered polypeptides, and methods of producing β-hydroxy-α-amino acids using engineered polypeptides. Compared to other processes of preparation, the use of the engineered polypeptides for the preparation of β-hydroxy-α-amino acids results in high purity of the desired stereoisomers, mild reaction conditions, low pollution and low energy consumption. It has good industrial application prospects.

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.