51591-89-0

Basic information

• Product Name: [S(R*,R*)]-2-amino-1-[p-(methylsulphonyl)phenyl]propane-1,3-diol
• Synonyms: [S(R*,R*)]-2-amino-1-[p-(methylsulphonyl)phenyl]propane-1,3-diol;(1S,2S)-2-Amino-1-[4-(methylsulfonyl)phenyl]-1,3-propanediol;Einecs 257-309-0
• CAS NO: 51591-89-0
• Molecular Formula: C₁₀H₁₅NO₄S
• Molecular Weight: 245.2954
• EINECS: 257-309-0
• Mol File: 51591-89-0.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 533.8°Cat760mmHg
• Flash Point: 276.6°C
• Appearance: /
• Density: 1.36g/cm³
• CAS DataBase Reference: [S(R*,R*)]-2-amino-1-[p-(methylsulphonyl)phenyl]propane-1,3-diol(CAS DataBase Reference)
• NIST Chemistry Reference: [S(R*,R*)]-2-amino-1-[p-(methylsulphonyl)phenyl]propane-1,3-diol(51591-89-0)
• EPA Substance Registry System: [S(R*,R*)]-2-amino-1-[p-(methylsulphonyl)phenyl]propane-1,3-diol(51591-89-0)

Safety Data

• Hazardous Substances Data: 51591-89-0(Hazardous Substances Data)

Usage

General Description

[S(R*,R*)]-2-amino-1-[p-(methylsulphonyl)phenyl]propane-1,3-diol, also known as amifostine, is a chemoprotective agent that is used to reduce the toxic effects of certain chemotherapy drugs on normal tissues. It is a prodrug that is activated by alkaline phosphatase in the body, and it works by scavenging free radicals and protecting healthy cells from damage. Amifostine has been shown to reduce the risk of side effects such as kidney damage and nerve damage that can be caused by certain cancer treatments. It is typically administered by injection before chemotherapy and has been approved for use in the United States and other countries for cancer patients undergoing specific types of treatment.

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

Upstream product

• 7780-07-6 (+/-)-threo and (+/-)-erythro-1-p-methanosulfonylphenyl-2-dichloroacetamido-1,3-propanediol 
• 36983-12-7 D-threo-p-methylsulfonylphenylserine ethyl ester 
• 108565-01-1 N-[1-hydroxymethyl-2-(4-methanesulfonyl-phenyl)-2-oxo-ethyl]-acetamide 
• 38423-42-6 N-[1-hydroxymethyl-2-(4-methylsulfanyl-phenyl)-2-oxo-ethyl]-acetamide 
• 408352-71-6 2-amino-1-(4-(methylmercapto)phenyl)ethanone 
• 23150-33-6 (1RS,2RS)-2-acetylamino-1-(4-methylsulfanyl-phenyl)-propane-1,3-diol 
• 56739-66-3 N-(4-methanesulfonyl-phenacyl)-acetamide 
• 96795-22-1 (4S,5S)-4-Hydroxymethyl-5-(4-methanesulfonyl-phenyl)-oxazolidin-2-one 
• 847-25-6 (+/-)-Thiamphenicol 
• 14052-59-6 D-threo-1-p-methylmercaptophenyl-2-dichloroacetamidopropane-1,3-diol 
• 119293-92-4 (+/-)-2-dichloroacetamido-β-hydroxy-4-methylmercaptopropiophenone 
• 39031-11-3 (1RS,2RS)-2-amino-1-(4-methanesulfonyl-phenyl)-propane-1,3-diol 
• 115475-67-7 Benzoic acid (S)-(4-methanesulfonyl-phenyl)-((S)-2-oxo-oxazolidin-4-yl)-methyl ester 
• 91645-98-6 (1RS,2RS)-2-acetylamino-1-(4-methanesulfonyl-phenyl)-propane-1,3-diol 

Downstream Products

• 847-25-6 (+/-)-Thiamphenicol 
• 51458-28-7 (1R,2R)-2-amino-1-<4-(methylsulphonyl)phenyl>-1,3-propanediol 
• 19934-71-5 2,2-dichloro-N-{1,3-dihydroxy-1-[4-(methylsulfonyl)phenyl]propan-2-yl}acetamide 

Relevant articles and documents

Preparation method of florfenicol

The invention relates to a preparation method of florfenicol, which belongs to the technical field of medicine synthesis. The preparation method adopts D-p-methylsulfonyl-phenylserine ethyl ester as a raw material to be subjected to reducing reaction, cyclization reaction, fluoridation and hydrolytic reaction to prepare the florfenicol. In the fluoridation, dichloromethane is used as a solvent, a cyclization product and a fluoridation reagent are used as reaction raw materials, and the mass ratio of the cyclization product to the fluoridation reagent is (1.25 to 1.30) to 1. The preparation method has the advantages of simple process operation and low cost. By controlling a reaction condition and using additives, byproducts of the fluoridation are reduced, so that a florfenicol product with high purity and fewer impurities can be obtained only by virtue of one-step decoloration and refining step, the product cost can be controlled, and the production efficiency can be improved.

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.