125354-93-0

Basic information

• Product Name: (2S,3S) methyl 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionate
• Synonyms: (2S,3S) methyl 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionate
• CAS NO: 125354-93-0
• Molecular Weight: 363.391
• Mol File: 125354-93-0.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: (2S,3S) methyl 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionate(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S) methyl 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionate(125354-93-0)
• EPA Substance Registry System: (2S,3S) methyl 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylthio)propionate(125354-93-0)

Safety Data

• Hazardous Substances Data: 125354-93-0(Hazardous Substances Data)

Upstream product

• 4875-10-9 o-nitrothiophenol 
• 126060-70-6 (2R,3R)-3-(4-Methoxy-phenyl)-oxirane-2-carboxylic acid methyl ester 
• 94098-21-2 methyl (2RS,3RS)-2-acetoxy-3-(p-methoxyphenyl)-3-(o-nitrophenylthio)propanoate 
• 125263-58-3 methyl (2RS,3RS)-2-chloroacetoxy-3-(p-methoxyphenyl)-3-(o-nitrophenylthio)propanoate 
• 96125-49-4 methyl trans-3-(4-methoxyphenyl)glycidate 
• 42245-42-1 methyl (2-RS,3-SR)-2,3-epoxy-3-(4-methoxyphenyl)propanoate 
• 123-11-5 4-methoxy-benzaldehyde 
• 127347-52-8 (2S,3R)-3-Hydroxy-3-(4-methoxy-phenyl)-2-(2,4,6-trichloro-benzenesulfonyloxy)-propionic acid methyl ester 
• 122517-80-0 (2S,3R)-(-)-methyl 2,3-dihydroxy-3-(p-methoxyphenyl)propionate 
• 30067-00-6 methyl (2RS,3RS)-2-hydroxy-3-(p-methoxyphenyl)-3-(o-nitrophenylthio)propanoate 
• 22755-25-5 o-nitrobenzenethiol sodium salt 
• 53100-99-5 methyl 3-chloro-3-(4-methoxyphenyl)-2-oxopropionate 
• 86603-46-5 3-(4-methoxy-phenyl)-3-(2-nitro-phenylsulfanyl)-2-oxo-propionic acid methyl ester 
• 20445-33-4 (R)-methoxytrifluoromethylphenylacetyl chloride 

Downstream Products

• 125354-94-1 methyl (2R,3R)-2-hydroxy-3-(p-methoxyphenyl)-3-(o-nitrophenylthio)propanoate 
• 30842-47-8 3t-hydroxy-2r-(4-methoxy-phenyl)-5-methyl-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-one 
• 42399-48-4 (2S,3S)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)-propionic acid 
• 30193-56-7 (2R,3S)-3-(2-Amino-phenylsulfanyl)-2-hydroxy-3-(4-methoxy-phenyl)-propionic acid methyl ester 
• 125263-58-3 methyl (2RS,3RS)-2-chloroacetoxy-3-(p-methoxyphenyl)-3-(o-nitrophenylthio)propanoate 
• 94098-21-2 methyl (2RS,3RS)-2-acetoxy-3-(p-methoxyphenyl)-3-(o-nitrophenylthio)propanoate 
• 42399-45-1 (2S,3S)-2-hydroxy-3-(p-methoxyphenyl)-3-(o-nitrophenylthio)propanoic acid 
• 99109-07-6 (+)-(2S,3S)-2-hydroxy-3-(4-methoxyphenyl)-3-(2-aminophenylthio)propanoic acid methyl ester 
• 27068-88-8 (+/-)-trans-2,3-dihydro-3-hydroxy-2-(4-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one 

Relevant articles and documents

Novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one via bakers' yeast reduction

A novel protocol for the asymmetric synthesis of 3-hydroxy-2-(4-methoxyphenyl)-2,3-dihydro-1,5-benzothiazepin-4(5H)-one is reported. Darzens condensation reactions of anisaldehyde with dichloroacetates, followed substitution reaction of sodium o-nitrophenylthiolate and bakers' yeast reduction furnished 2-hydroxy-3-(4-methoxyphenyl)-3-(2-nitrophenylsulfanyl)-propionates. Further reduction of a nitro group and cyclization gave the title compound.

Enzymatic hydrolysis in organic solvents for kinetic resolution of water-insoluble α-acyloxy esters with immobilized lipases

Enantioselective hydrolysis of water-insoluble α-acyloxy esters, (±)- 5 and (±)-6, was carried out using lipases immobilized with Celite or a synthetic prepolymer (ENTP-4000 or ENT-4000) in a water-saturated organic solvent to produce chiral intermediates, (2S,3S)-5 and (2S,3R)-4, for the synthesis of diltiazem hydrochloride 1 and (-)-indolmycin 2, respectively. Furthermore, enantioselective hydrolysis of (±)-6 using lipid-lipase aggregates in water-saturated organic solvent was also found to give (2S,3R)- 4.

ENZYMATIC HYDROLYSIS IN ORGANIC SOLVENTS FOR KINETIC RESOLUTION OF WATER-INSOLUBLE α-ACYLOXY ESTERS WITH IMMOBILIZED LIPASES

Asymmetric hydrolysis of water-insoluble α-acyloxy esters, (+/-)-5 and (+/-)-6, was carried out using lipases immobilized with celite or synthetic prepolymer (ENTP-4000 or ENT-4000) in water-saturated organic solvent to produce chiral intermediates, (2S,3