19934-71-5

Basic information

• Product Name: Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsul fonyl)phenyl)ethyl)-, (S-(R*,R*))-
• Synonyms: Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsul fonyl)phenyl)ethyl)-, (S-(R*,R*))-;2,2-dichloro-N-[(1S,2S)-1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan -2-yl]acetamide;ent-ThiaMphenicol;L-threo-2,2-Dichloro-N-[β-hydroxy-α-(hydroxyMethyl)-p-(Methylsulfonyl)phenethyl]AcetaMide;ThiaMphenicol EpiMer;Win 5063-3
• CAS NO: 19934-71-5
• Molecular Formula: C₁₂H₁₅Cl₂NO₅S
• Molecular Weight: 356.22
• Mol File: 19934-71-5.mol

Chemical Properties

• Boiling Point: 695.9°Cat760mmHg
• Flash Point: 374.7°C
• Appearance: /
• Density: 1.491g/cm³
• Vapor Pressure: 2.5E-20mmHg at 25°C
• Refractive Index: 1.582
• CAS DataBase Reference: Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsul fonyl)phenyl)ethyl)-, (S-(R*,R*))-(CAS DataBase Reference)
• NIST Chemistry Reference: Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsul fonyl)phenyl)ethyl)-, (S-(R*,R*))-(19934-71-5)
• EPA Substance Registry System: Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-(methylsul fonyl)phenyl)ethyl)-, (S-(R*,R*))-(19934-71-5)

Safety Data

• Hazardous Substances Data: 19934-71-5(Hazardous Substances Data)

Usage

Uses

The enatiomeric analogue of the antimicrobial agent Thiamphenicol (T344160).

InChI:InChI=1/C12H15Cl2NO5S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-16)15-12(18)11(13)14/h2-5,9-11,16-17H,6H2,1H3,(H,15,18)/t9-,10-/m0/s1

Upstream product

• 1768-31-6 pentachloroacetone 
• 51591-89-0 (1S,2S)-2-amino-1-(4-(methylsulfonyl)phenyl)propane-1,3-diol 
• 74-88-4 methyl iodide 
• 38423-42-6 N-[1-hydroxymethyl-2-(4-methylsulfanyl-phenyl)-2-oxo-ethyl]-acetamide 
• 39031-11-3 (1RS,2RS)-2-amino-1-(4-methanesulfonyl-phenyl)-propane-1,3-diol 
• 119293-92-4 (+/-)-2-dichloroacetamido-β-hydroxy-4-methylmercaptopropiophenone 
• 31925-27-6 DL-threo-p-methylsulfonylphenylserine ethyl ester 
• 108565-01-1 N-[1-hydroxymethyl-2-(4-methanesulfonyl-phenyl)-2-oxo-ethyl]-acetamide 
• 408352-71-6 2-amino-1-(4-(methylmercapto)phenyl)ethanone 
• 91645-98-6 (1RS,2RS)-2-acetylamino-1-(4-methanesulfonyl-phenyl)-propane-1,3-diol 
• 23150-33-6 (1RS,2RS)-2-acetylamino-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol 
• 56739-66-3 N-(4-methanesulfonyl-phenacyl)-acetamide 
• 115475-67-7 Benzoic acid (S)-(4-methanesulfonyl-phenyl)-((S)-2-oxo-oxazolidin-4-yl)-methyl ester 
• 96795-22-1 (4S,5S)-4-Hydroxymethyl-5-(4-methanesulfonyl-phenyl)-oxazolidin-2-one 

Downstream Products

• 51591-89-0 (1S,2S)-2-amino-1-(4-(methylsulfonyl)phenyl)propane-1,3-diol 
• 39031-11-3 (1RS,2RS)-2-amino-1-(4-methanesulfonyl-phenyl)-propane-1,3-diol 

Relevant articles and documents

An Efficient Stereoselective Total Synthesis of All Stereoisomers of the Antibiotic Thiamphenicol through Ruthenium-Catalyzed Asymmetric Reduction by Dynamic Kinetic Resolution

Thiamphenicol is a widely used antibiotic that exhibits activity against numerous Gram-positive and Gram-negative pathogens. Here, we describe the expedient synthesis of its four stereoisomers through a dynamic kinetic resolution that follows a ruthenium-catalyzed asymmetric hydrogenation or a hydrogen transfer reaction as the key step.

CYCLOFUNCTIONALISATION REACTIONS OF EPOXYALCOHOL DERIVATIVES. 3. CYCLISATION-ACYL MIGRATION OF N-BENZOYLCARBAMATES TO STEREODEFINED OXAZOLIDINONES. A NEW, DIASTEREOSPECIFIC ROUTE TO THIAMPHENICOL.

N-Benzoylcarbamates formed in situ from 2,3-epoxyalcohols and PhCONCO undergo clean to C-2 cyclisation followed by N to O acyl migration on treatment with catalytic sodium imidazolide or other bases.Subsequent benzoate cleavage (NaOMe) is accompanied by equilibration of the N-unsubstituted oxazolidinones; cleavage without significant isomerisation is achieved with MeLi or Zn(BH4)2.This methodology is applied in a diastereospecific, 6-step conversion of methyl 4-bromophenyl sulfonate to racemic Thiamphenicol.