146452-40-6

Basic information

• Product Name: (2R,3R) ethyl 2-chloro-3-hydroxy-3-phenylpropionate
• Synonyms: (2R,3R) ethyl 2-chloro-3-hydroxy-3-phenylpropionate
• CAS NO: 146452-40-6
• Molecular Weight: 228.675
• Mol File: 146452-40-6.mol
• Article Data: 10

Chemical Properties

• CAS DataBase Reference: (2R,3R) ethyl 2-chloro-3-hydroxy-3-phenylpropionate(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R) ethyl 2-chloro-3-hydroxy-3-phenylpropionate(146452-40-6)
• EPA Substance Registry System: (2R,3R) ethyl 2-chloro-3-hydroxy-3-phenylpropionate(146452-40-6)

Safety Data

• Hazardous Substances Data: 146452-40-6(Hazardous Substances Data)

Upstream product

• 100-52-7 benzaldehyde 
• 105-39-5 chloroacetic acid ethyl ester 
• 927-80-0 1-ethoxyacetylene 
• 68-12-2 N,N-dimethyl-formamide 
• 4192-77-2 ethyl cinnamate 
• 41381-97-9 ethyl 2-chloro-3-oxo-3-phenylpropionate 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 

Downstream Products

• 4192-77-2 ethyl cinnamate 
• 33401-74-0 ethyl (3R)-3-hydroxy-3-phenylpropionate 
• 121-39-1 (2S,3R)-ethyl 3-phenyloxirane-2-carboxylate 

Relevant articles and documents

Microbial reduction of 2-chloro-3-aryl-3-oxopropionic acid esters

2-Chloro-3-aryl-3-oxopropionic acid esters are reduced by microorganisms to syn- and/or anti-2-chloro-3-hydroxy-3-arylpropionates, in competition with dechlorination and decarboxylation reactions. Using selected strains, it is possible to obtain enantiomerically pure chlorohydroxyesters, which were converted to the corresponding phenylglycidic esters with high stereospecificity.

A new dehydrogenase from Clostridium acetobutylicum for asymmetric synthesis: Dynamic reductive kinetic resolution entry into the Taxotere side chain

An NADP-dependent alcohol dehydrogenase from Clostridium acetobutylicum (CaADH) has been expressed and characterized. CaADH enantioselectively reduces aromatic α-, β- and γ-keto esters to the corresponding d-hydroxy esters and provides a building block for the Taxotere side chain (95% yield, 95% de, 99% ee) by dynamic reductive kinetic resolution (DYRKR).

Synthesis of Novel Diastereomeric Diphosphine Ligands and Their Applications in Asymmetric Hydrogenation Reactions

(Matrix Presented) Diastereomeric biaryl diphosphine ligands 10 and 11 with added chiral centers on the backbone were synthesized. Substrate-directed asymmetric synthesis occurred in the coupling step of the preparation of the diastereomeric diphosphine oxides. The diastereomeric diphosphine oxides were easily separated by column chromatography with silica gel. Ruthenium catalysts containing these ligands were highly effective in the hydrogenation of 2-(6′-methoxy-2′-naphthyl)propenoic acid and β-ketoesters. The additional chiral centers had a significant influence on the enantioselectivity and activity of the catalysts.