96795-22-1

Basic information

• Product Name: (4R,5R)-4-hydroxymethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone
• Synonyms: (4R,5R)-4-hydroxymethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone
• CAS NO: 96795-22-1
• Molecular Weight: 271.294
• Mol File: 96795-22-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (4R,5R)-4-hydroxymethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5R)-4-hydroxymethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone(96795-22-1)
• EPA Substance Registry System: (4R,5R)-4-hydroxymethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone(96795-22-1)

Safety Data

• Hazardous Substances Data: 96795-22-1(Hazardous Substances Data)

Upstream product

• 96795-21-0 (4R,5R)-4-hydroxymethyl-5-<4-(methylthio)phenyl>-2-oxazolidinone 
• 5398-77-6 para-methanesulfonylbenzaldehyde 
• 256475-83-9 (2S,3R)-methyl-2-amino-3-[4-(methylsulfonyl)phenyl]-3-hydroxy-propanoate 
• 31925-29-8 (2S,3R)-2-amino-3-hydroxy-3-(4-methylsulfonylphenyl)propionic acid ethyl ester 
• 75-44-5 phosgene 
• 96795-20-9 (1R,2R)-2-ethoxycarbonylamino-1-<4-(methylthio)phenyl>-1,3-propanediol 
• 51458-28-7 (1R,2R)-2-amino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol 
• 23150-35-8 (R*,R*)-(+)-thiomicamine 
• 914646-16-5 (S)-1-[4-(methylsulfonyl)phenyl]-2-propen-1-ol 
• 701935-65-1 1-[4-(methylsulfonyl)phenyl]-2-propen-1-ol 
• 701935-64-0 1-[4-(methylsulfanyl)phenyl]-2-propen-1-ol 
• 3446-89-7 4-(Methylthio)benzaldehyde 
• 914646-18-7 (S)-1-[4-(methylsulfonyl)phenyl]allyl carbamate 
• 108656-26-4 (1R,2R)-2-ethoxycarbonylamino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol 

Downstream Products

• 15318-45-3 thiamphenicol 
• 73231-34-2 Florfenicol 
• 108656-27-5 (1R,2S)-2-(2,3-dimethylbenzoyl)amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol 
• 108656-29-7 (4S,5R)-N-(2,3-dimethylbenzoyl)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone 
• 76639-93-5 (1R,2S)-2-amino-3-fluoro-1-<4-(methylsulphonyl)phenyl>-1-propanol 
• 847-25-6 (+/-)-Thiamphenicol 
• 108656-28-6 (4S,5R)-4-fluoromethyl-5-<4-(methylsulphonyl)phenyl>-2-oxazolidinone 
• 39031-11-3 (1RS,2RS)-2-amino-1-(4-methanesulfonyl-phenyl)-propane-1,3-diol 

Relevant articles and documents

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.

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.

2-OXAZOLIDINONES AS REGIOSELECTIVE PROTECTION OF β-AMINO ALCOHOLS IN THE SYNTHESIS OF 2-AMINO-1-ARYL-3-FLUORO-1-PROPANOLS

The regioselective conversion of threo-2-ethoxycarbonylamino-1--1,3-propanediol, 4, into 4-hydroxymethyl-5--2-oxazolidinone, 8, is described as well as the use of this protection procedure in the synthesis of the fluoro analogue, 2, of thiamphenicol, 1.Methods of hydrolysis of the oxazolidinone ring are revisited for compound 11; new procedures via N-acylated intermediates have been investigated and their application is reported.