4302-89-0Relevant articles and documents
Synthesis of 4-sulfur-substituted (2S,3R)-3-phenylserines by enzymatic resolution. Enantionure precursors for thiamphenicol and florfenicol
Kaptein, Bernard,Van Dooren, Thei J.G.M.,Boesten, Wilhelmus H. J.,Sonke, Theo,Duchateau, Alexander L.L.,Broxterman, Quirinus B.,Kamphuis, Johan
, p. 10 - 17 (2013/09/08)
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.
Asymmetric synthesis of the antibiotic (+)-thiamphenicol using cis-N-(p-toluenesulfinyl)aziridine 2-carboxylic acids
Davis, Franklin A.,Zhou, Ping
, p. 7525 - 7528 (2007/10/02)
A concise, highly efficient asymmetric synthesis of aminopropanediol (1R,2R)-(-)-3, precursor to the broad spectrum antibiotics thiamphenicol/florfenicol 1/2, was prepared in two steps from cis-aziridine 2-carboxylic acid (2S,3S)-(-)-5.