51458-28-7

Basic information

• Product Name: [R(R*,R*]-2-amino-1-[p-(methylsulphonyl)phenyl]propane-1,3-diol
• Synonyms: [R(R*,R*]-2-amino-1-[p-(methylsulphonyl)phenyl]propane-1,3-diol;Aminodiol Sulfone;Thiamphenicol Sulfone Amine;(1R,2R)-2-AMINO-1-(4-METHYLSULFONYLPHENYL)PROPANE-1,3-DIOL;D-(-)-THREO-2-AMINO-1-[4-METHYLSULFONYL)PHENYL]-1,3-PROPANEDIOLFLORFENICOL;(1R,2R)-1-[4-(Methylsulfonyl)phenyl]-2-amino-1,3-propanediol;(1R,2R)-2-Amino-1-[4-(methylsulfonyl)phenyl]-1,3-propanediol;(2R,3R)-2-Amino-3-[4-(methylsulfonyl)phenyl]-1,3-propanediol
• CAS NO: 51458-28-7
• Molecular Formula: C₁₀H₁₅NO₄S
• Molecular Weight: 245.2954
• EINECS: 257-216-5
• Mol File: 51458-28-7.mol
• Article Data: 20

Chemical Properties

• Boiling Point: 533.8 °C at 760 mmHg
• Flash Point: 276.6 °C
• Appearance: /
• Density: 1.36 g/cm³
• Vapor Pressure: 3.17E-12mmHg at 25°C
• Refractive Index: 1.588
• CAS DataBase Reference: [R(R*,R*]-2-amino-1-[p-(methylsulphonyl)phenyl]propane-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: [R(R*,R*]-2-amino-1-[p-(methylsulphonyl)phenyl]propane-1,3-diol(51458-28-7)
• EPA Substance Registry System: [R(R*,R*]-2-amino-1-[p-(methylsulphonyl)phenyl]propane-1,3-diol(51458-28-7)

Safety Data

• Hazardous Substances Data: 51458-28-7(Hazardous Substances Data)

Usage

General Description

[R(R*,R*]-2-amino-1-[p-(methylsulphonyl)phenyl]propane-1,3-diol is a compound that is also known as l-sotalol. It is a medication that is used to treat cardiac arrhythmias, specifically atrial fibrillation and ventricular tachycardia. L-sotalol belongs to the class of drugs known as beta-blockers, which work by blocking the effects of adrenaline on the heart. This helps to regulate the heart rhythm and reduce the risk of potentially dangerous arrhythmias. L-sotalol is also used off-label for the treatment of certain types of heart failure and hypertension. It is available in the form of tablets and is typically taken orally. L-sotalol should be used with caution in patients with certain heart conditions and may cause side effects such as dizziness, fatigue, and nausea. It is important to follow the dosage and usage instructions provided by a healthcare professional when taking this medication.

InChI:InChI=1/C10H15NO4S/c1-16(14,15)8-4-2-7(3-5-8)10(13)9(11)6-12/h2-5,9-10,12-13H,6,11H2,1H3/t9-,10-/m1/s1

Upstream product

• 15318-45-3 thiamphenicol 
• 39031-11-3 (1RS,2RS)-2-amino-1-(4-methanesulfonyl-phenyl)-propane-1,3-diol 
• 119293-92-4 (+/-)-2-dichloroacetamido-β-hydroxy-4-methylmercaptopropiophenone 
• 14052-59-6 D-threo-1-p-methylmercaptophenyl-2-dichloroacetamidopropane-1,3-diol 
• 946859-86-5 tert-butyl N-[(1R,2R)-1,3-dihydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]carbamate 
• 56739-66-3 N-(4-methanesulfonyl-phenacyl)-acetamide 
• 23150-33-6 (1RS,2RS)-2-acetylamino-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol 
• 408352-71-6 2-amino-1-(4-(methylmercapto)phenyl)ethanone 
• 38423-42-6 N-[1-hydroxymethyl-2-(4-methylsulfanyl-phenyl)-2-oxo-ethyl]-acetamide 
• 108565-01-1 N-[1-hydroxymethyl-2-(4-methanesulfonyl-phenyl)-2-oxo-ethyl]-acetamide 
• 115475-67-7 Benzoic acid (S)-(4-methanesulfonyl-phenyl)-((S)-2-oxo-oxazolidin-4-yl)-methyl ester 
• 31925-27-6 DL-threo-p-methylsulfonylphenylserine ethyl ester 
• 338-69-2 D-Alanine 
• 5398-77-6 para-methanesulfonylbenzaldehyde 

Downstream Products

• 15318-45-3 thiamphenicol 
• 847-25-6 (+/-)-Thiamphenicol 
• 51591-89-0 (1S,2S)-2-amino-1-(4-(methylsulfonyl)phenyl)propane-1,3-diol 
• 76639-91-3 (1R,2R)-1-<4-(methylsulphonyl)phenyl>-2-phthalimido-1,3-propanediol 
• 108656-26-4 (1R,2R)-2-ethoxycarbonylamino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol 
• 96795-00-5 D-threo-4,5-dihydro-5-(4-methylsulphonylphenyl)-2-phenyl-4-oxazolemethanol 
• 96795-16-3 (1R,2R)-3-acetoxy-1-<4-(methylsulphonyl)phenyl>-2-phthalimido-1-propanol 
• 126813-11-4 D-threo-2-(dichloromethyl)-5-(4-methanesulfonylphenyl)-4,5-dihydro-1,3-oxazol-4-yl methanol 
• 96795-01-6 C₁₃H₁₅Cl₂NO₆S₂ 
• 1258542-72-1 (1R,2R)-1-(4-methylsulfonylphenyl)-2-(Nα-Boc-L-methionylsulfone-amido)-1,3-propadiol 
• 129126-23-4 D-(-)-threo-1-(4-(methylsulfonyl)phenyl)-2-amino-3-chloro-1-propanol hydrochloride 
• 129126-22-3 D-(-)-threo-2-phenyl-4-(chloromethyl)-5-(4-(methylsulfonyl)phenyl)-2-oxazoline 
• 126428-97-5 D-(-)-threo-2-phenyl-4-(fluoromethyl)-5-(4-(methylsulfonyl)phenyl)-2-oxazoline 

Relevant articles and documents

Catalytic Syn-Selective Nitroaldol Approach to Amphenicol Antibiotics: Evolution of a Unified Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, (+)-Thiamphenicol, and (+)-Florfenicol

A unified strategy for an efficient and high diastereo- and enantioselective synthesis of (-)-chloramphenicol, (-)-azidamphenicol, (+)-thiamphenicol, and (+)-florfenicol based on a key catalytic syn-selective Henry reaction is reported. The stereochemistry of the ligand-enabled copper(II)-catalyzed aryl aldehyde Henry reaction of nitroethanol was first explored to forge a challenging syn-2-amino-1,3-diol structure unit with vicinal stereocenters with excellent stereocontrol. Multistep continuous flow manipulations were carried out to achieve the efficient asymmetric synthesis of this family of amphenicol antibiotics.

One-Pot Asymmetric Synthesis of an Aminodiol Intermediate of Florfenicol Using Engineered Transketolase and Transaminase

Florfenicol is the 3′-fluoro derivative of thiamphenicol and has been widely used in veterinary medicine for its high antibacterial activity and safety. However, the development of simplified and environmentally friendly catalytic methods for the stereoselective production of florfenicol is a key challenge. Herein, we established a highly stereoselective enzymatic one-pot reaction for the synthesis of an aminodiol intermediate of florfenicol bearing two stereocenters from industrial raw material 4-(methylsulfonyl) benzaldehyde by coupling transketolase (TK) and ω-transaminase (TA). The enantioselectivity of TK from E. coli was converted from (S) (93% ee) to (R) (95% ee), and we also inverted the enantiopreference (E(S) = 9 to E(R) = 12) and ketone/aldehyde substrate selectivity of TA ATA117 via structure-guided enzyme engineering. Docking calculations and molecular dynamics simulations of the wild-type and mutant enzymes unveiled the molecular basis for enzymatic stereocontrol. Using the engineered TK and TA, (1R,2R)-p-methylsulfonyl phenylserinol was biosynthesized with good yield (76%) and high stereoselectivity (96% de and >99% ee). Our work established an enzymatic synthetic route to (1R,2R)-p-methylsulfonyl phenylserinol, facilitating the development of a chemoenzymatic method for producing florfenicol.

Preparation method of florfenicol intermediate (by machine translation)

The compound is obtained by carrying out asymmetric addition reaction with nitroethanol under the catalysis of Cu (OTf) and a copper salt complex formed by chiral ligand L, and then carrying out catalytic hydrogenation on palladium carbon . the compound is obtained after catalytic hydrogenation of palladium carbon. 2The route synthesis method is simple to operate, environmentally friendly, and wide in application prospect. (by machine translation)