139059-01-1

Basic information

• Product Name: (4S,5R)-5-(4-(methylsulfonyl)phenyl)-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid ethyl ester
• Synonyms: (4S,5R)-5-(4-(methylsulfonyl)phenyl)-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid ethyl ester
• CAS NO: 139059-01-1
• Molecular Weight: 373.43
• Mol File: 139059-01-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (4S,5R)-5-(4-(methylsulfonyl)phenyl)-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5R)-5-(4-(methylsulfonyl)phenyl)-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid ethyl ester(139059-01-1)
• EPA Substance Registry System: (4S,5R)-5-(4-(methylsulfonyl)phenyl)-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid ethyl ester(139059-01-1)

Safety Data

• Hazardous Substances Data: 139059-01-1(Hazardous Substances Data)

Upstream product

• 139059-00-0 (4R,5R)-5-(4-(methylsulfonyl)phenyl)-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid ethyl ester 
• 55-21-0 benzamide 
• 31925-29-8 (2S,3R)-2-amino-3-hydroxy-3-(4-methylsulfonylphenyl)propionic acid ethyl ester 
• 5333-86-8 ethyl benzimidate hydrochloride 
• 139235-94-2 ethyl (2R,3S)-3-(4-methylthiophenyl)serinate hydrochloride 
• 17087-39-7 DL-threo-3-(4-methylthiophenyl)serine 
• 139164-32-2 ethyl (2R,3S)-2-benzamido-3-hydroxy-3-(4-methylsulfonylphenyl)propionate 
• 139058-99-4 ethyl L-threo-N-benzoyl-3-(4-methylthiophenyl)serinate 
• 98-88-4 benzoyl chloride 

Downstream Products

• 96795-00-5 D-threo-4,5-dihydro-5-(4-methylsulphonylphenyl)-2-phenyl-4-oxazolemethanol 
• 31925-29-8 (2S,3R)-2-amino-3-hydroxy-3-(4-methylsulfonylphenyl)propionic acid ethyl ester 

Relevant articles and documents

Preparation method of (2S, 3R)-p-methylsulfonylphenyl serine ethyl ester

The invention provides a preparation method of (2S, 3R)-p-methylsulfonylphenyl serine ethyl ester. The preparation method comprises the following steps: dissolving p-methylsulfonyl benzaldehyde and 2-halogenated ethyl acetate serving as raw materials in a solvent A to prepare (2R, 3R)-2-halogen-3-hydroxy-3-(4-methylsulfonyl) phenyl ethyl propionate under the action of a catalyst A, substituting halogen atoms with azide, and performing catalytic hydrogenation reduction to prepare (2S, 3R)-p-methylsulfonyl phenyl serine ethyl ester; or using p-methylsulfonyl benzaldehyde and 2-halogenated ethylacetate as raw materials and dissolving in a solvent B, and preparing (2S, 3S)-2-halogen-3-hydroxy-3-(4-methylsulfonyl) phenyl ethyl propionate under the action of a catalyst B, substituting halogen atoms with benzamide, and preparing (2S, 3R)-p-methylsulfonyl phenyl serine ethyl ester through cyclization, configuration transformation and hydrolysis. The preparation method is high in product purity and high in yield.

An enzymatic route to florfenicol

Racemic ethyl threo-3-14-methylthiophenyl)serinate is resolved by enzymatic hydrolysis using protease from Streptomyces griseus and both stereoisomers are converted to D-threo-4,5-dihydro-5-(4-methylsulfonylphenyl)-2-phenyl-4-oxazolemethan ol, thereby giving a formal synthesis of florfenicol.