294637-52-8

Upstream product

• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 24393-61-1 ethyl (E)-3-(4-nitrophenyl)-2-propenoate 
• 294637-48-2 (4S,5R)-3-Benzoyl-5-(4-nitro-phenyl)-2-oxo-oxazolidine-4-carboxylic acid ethyl ester 
• 142917-83-7 (2S,3R)-2,3-Dihydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester 
• 914646-14-3 (S)-1-(4-nitrophenyl)allyl carbamate 
• 93856-93-0 [(1R,2R)-2-hydroxy-1-hydroxymethyl-2-(4-nitro-phenyl)-ethy]carbamic acid ethyl ester 
• 294637-50-6 ethyl (4S,5R)-5-(4-nitrophenyl)-2-oxooxazolidine-4-carboxylate 
• 914646-11-0 (S)-1-(4-nitrophenyl)-2-propen-1-ol 
• 123232-63-3 1-(4-nitrophenyl)-prop-2-en-1-ol 
• 555-16-8 4-nitrobenzaldehdye 

Downstream Products

• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 56-75-7 chloramphenicol 
• 13838-08-9 Azidamfenicol 

Relevant academic research and scientific papers

Unified Strategy to Amphenicol Antibiotics: Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, and (+)-Thiamphenicol and Its (+)-3-Floride

The asymmetric synthesis of (-)-chloramphenicol, (-)-azidamphenicol, and (+)-thiamphenicol and its (+)-3-floride, (+)-florfenicol, is reported. This approach toward the amphenicol antibiotic family features two key steps: (1) a cinchona alkaloid derived urea-catalyzed aldol reaction allows highly enantioselective access to oxazolidinone gem-diesters and (2) a continuous flow diastereoselective decarboxylation of thermally stable oxazolidinone gem-diesters to form the desired trans-oxazolidinone monoesters with two adjacent stereocenters that provide the desired privileged scaffolds of syn-vicinal amino alcohols in the amphenicol family.

Synthesis of isomeric 2-oxazolidinones from (1R,2R)-and (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediols

A synthesis is reported for (4R,5R)-and (4S,5S)-4-hydroxymethyl-5-(4- nitrophenyl)oxazolidin-2-ones and (1′R,4R)-and (1′S,4S)-4- [hydroxy(4-nitrophenyl)methyl]oxazolidin-2-ones from (1R,2R)-and (1S,2S)-2-amino-1-(4-nitrophenyl)-1,3-propanediols. The effect of the experimental conditions on the formation of these compounds was studied.

A short enantioselective synthesis of (-)-chloramphenicol and (+)-thiamphenicol using tethered aminohydroxylation

An efficient enantioselective synthesis of (-)-chloramphenicol (1) and (+)-thiamphenicol (2) is described. These antibiotics have been synthesized from commercially available 4-nitrobenzaldehyde and 4-(methylthio)benzaldehyde, respectively, using tethered aminohydroxylation and Sharpless asymmetric epoxidation as the chirality inducing steps.

Modified Mg: Al hydrotalcite in the synthesis of oxazolidin-2-ones

The modified Mg: Al (3: 1) hydrotalcite has been found to be an efficient catalyst in the conversion of carbamates into oxazolidin-2-ones under mild reaction conditions. A wide variety of oxazolidin-2-ones were obtained with excellent chemical yield. The Royal Society of Chemistry 2005.

Synthetic applications of the cyclic iminocarbonate rearrangement Enantioselective syntheses of chloramphenicol and 4-epi-cytoxazone

Chloramphenicol and 4-epi-cytoxazone have been enantioselectively synthesized using the asymmetric dihydroxylation and the cyclic iminocarbonate rearrangement as key steps. (C) 2000 Elsevier Science Ltd.