23150-29-0

Basic information

• Product Name: (2S,3R)-2-amino-3-hydroxy-3-(4-mercaptomethylbenzene)propanoic acid
• Synonyms: (2S,3R)-2-amino-3-hydroxy-3-(4-mercaptomethylbenzene)propanoic acid
• CAS NO: 23150-29-0
• Molecular Weight: 227.284
• Mol File: 23150-29-0.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (2S,3R)-2-amino-3-hydroxy-3-(4-mercaptomethylbenzene)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-2-amino-3-hydroxy-3-(4-mercaptomethylbenzene)propanoic acid(23150-29-0)
• EPA Substance Registry System: (2S,3R)-2-amino-3-hydroxy-3-(4-mercaptomethylbenzene)propanoic acid(23150-29-0)

Safety Data

• Hazardous Substances Data: 23150-29-0(Hazardous Substances Data)

Upstream product

• 3446-89-7 4-(Methylthio)benzaldehyde 
• 17087-39-7 DL-threo-3-(4-methylthiophenyl)serine 
• 100370-88-5 ethyl DL-threo-3-(4-methylthiophenyl)serinate hydrochloride 

Downstream Products

• 23150-35-8 (R*,R*)-(+)-thiomicamine 
• 96795-00-5 D-threo-4,5-dihydro-5-(4-methylsulphonylphenyl)-2-phenyl-4-oxazolemethanol 
• 139058-99-4 ethyl L-threo-N-benzoyl-3-(4-methylthiophenyl)serinate 
• 139164-32-2 ethyl (2R,3S)-2-benzamido-3-hydroxy-3-(4-methylsulfonylphenyl)propionate 
• 139164-31-1 methyl D-threo-3-(4-methylthiophenyl)serinate hydrochloride 
• 23150-30-3 (2R,3S)-3-[4-(methylthio)phenyl]serine 
• 139059-01-1 (4S,5R)-5-(4-(methylsulfonyl)phenyl)-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid ethyl ester 
• 139059-00-0 (4R,5R)-5-(4-(methylsulfonyl)phenyl)-2-phenyl-4,5-dihydrooxazole-4-carboxylic acid ethyl ester 
• 139235-94-2 ethyl (2R,3S)-3-(4-methylthiophenyl)serinate hydrochloride 
• 100370-88-5 ethyl DL-threo-3-(4-methylthiophenyl)serinate hydrochloride 

Relevant articles and documents

Synthesis of 4-sulfur-substituted (2S,3R)-3-phenylserines by enzymatic resolution. Enantionure precursors for thiamphenicol and florfenicol

Enantiomerically pure 4-methylthio- and 4-methylsulfonylsubstitutcd (2S,3R)-3-phenylserines are prepared by enzymatic resolution of the corresponding racemic threo amides using the amidase from Ochrobactrum anthropi NCIMB 40321. The unwanted (2R,3S) enantiomers of the amides are separated from the enantiopure amino acids and easily racemized after Schiff base formation with the corresponding 4-(methylthio)- and 4-(methylsulfonyl)benzaldehyde. The racemization can be combined with the preparation of the racemic amides by aldol reaction under crystallization conditions to yield only the threo isomers. Enantiopure (25,3R)-3-[4-(methylthio)phenyl]serine and (2S,3R)-3-[4-(methylsulfonyl)phenyl]serine are thus obtained in 78% and 62% overall yields starting from the corresponding substituted benzaldehydes. (2S,3A)-3-[4-(Methylthio)phenyl]serine is reduced to (1R,2R)-2-amino-1-[4-(methylthio)phenyl]propane-1,3-diol with NaBH4/H2SO4 and can be used for the synthesis of thiamphenicol and florfenicol.