51259-82-6

Basic information

• Product Name: (1R,2R)-1,3-diacetoxy-2-acetylamino-1-(4-nitro-phenyl)-propane
• Synonyms: (1R,2R)-1,3-diacetoxy-2-acetylamino-1-(4-nitro-phenyl)-propane
• CAS NO: 51259-82-6
• Molecular Weight: 338.317
• Mol File: 51259-82-6.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (1R,2R)-1,3-diacetoxy-2-acetylamino-1-(4-nitro-phenyl)-propane(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,2R)-1,3-diacetoxy-2-acetylamino-1-(4-nitro-phenyl)-propane(51259-82-6)
• EPA Substance Registry System: (1R,2R)-1,3-diacetoxy-2-acetylamino-1-(4-nitro-phenyl)-propane(51259-82-6)

Safety Data

• Hazardous Substances Data: 51259-82-6(Hazardous Substances Data)

Upstream product

• 111136-67-5 (1R,2R)-2-acetamido-1-phenylpropane-1,3-diyl diacetate 
• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 108-24-7 acetic anhydride 
• 46032-98-8 (1R,2R)-2-amino-1-phenylpropane-1,3-diol 
• 115794-67-7 methyl (2R,3S)-3-phenylglycidate 
• 849357-83-1 (2R,3R)-2-Hydroxy-3-nitrosooxy-3-phenyl-propionic acid methyl ester 
• 849357-84-2 (2S,3R)-2-Azido-3-nitrosooxy-3-phenyl-propionic acid methyl ester 
• 439797-74-7 (1R,2R)-1,3-diacetoxy-2-amino-1-phenyl-propane 
• 3509-75-9 (1RS,2SR)-1,3-diacetoxy-2-acetylamino-1-phenyl-propane 
• 3509-75-9 (1RS,2RS)-1,3-diacetoxy-2-acetylamino-1-phenyl-propane 
• 74104-28-2 α-acetamido-β-hydroxypropiophenone 
• 3306-06-7 (+/-)-threo-2-amino-1-phenyl-1,3-propanediol 
• 108943-99-3 N-(1-acetoxy-3-oxo-3-phenylpropyl)acetamide 
• 40958-11-0 (1RS,2RS)-3-acetoxy-2-acetylamino-1-(4-nitro-phenyl)-propan-1-ol 

Downstream Products

• 56-75-7 chloramphenicol 
• 56-75-7 2-(2,2-dichloroacetylamino)-1-(4-nitrophenyl)propane-1,3-diol 
• 119-62-0 (1S,2S)-2-amino-1-(4-nitrophenyl)propane-1,3-diol 
• 119-62-0 (1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol 
• 134-90-7 L-threo-chloramphenicol 
• 56-75-7 chlorampenicol 
• 1885-08-1 (1RS,2RS)-2-acetylamino-1-(4-nitro-phenyl)-propane-1,3-diol 
• 119-62-0 (+/-)-threo-1-(4-nitro-phenyl)-2-amino-1,3-propanediol 
• 1885-08-1 (1RS,2RS)-2-acetylamino-1-(4-nitro-phenyl)-propane-1,3-diol 
• 119-62-0 (1RS,2SR)-2-amino-1-(4-nitro-phenyl)-propane-1,3-diol 
• 4423-58-9 N-(1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)acetamide 

Relevant articles and documents

An Acyl Transfer Reaction Catalyzed by an Epimerase MarH

MarH, a small protein (129 amino acids) belonging to the cupin superfamily, was previously characterized as an epimerase involved in the (2S,3S)-β-methyltryptophan formation in the maremycin biosynthesis. Here, MarH was discovered to act as an acyltransferase that can catalyze the 3-O-acylation of chloramphenicol. Furthermore, MarH can catalyze N-acylation of deacylated chloramphenicol analogue thereby activating them for 3-O-acylation. By systematic site-directed mutagenesis, H64 was revealed as a potential catalytic base that deprotonates the acyl acceptor substrate. Nucleophilic attack at the carbonyl carbon of the acyl donor then gives the acylation product.

Stereoselective synthesis of chloramphenicol from D-serine

An efficient synthesis of the widely used antibiotic chloramphenicol (1) is described. The key step in the synthesis involves chelation-controlled addition of phenylmagnesium bromide to a suitably protected D-serinal derivative, affording the pivotal D-threo 1,2-amino alcohol intermediate 3 in a highly stereoselective manner.