285130-47-4

Basic information

• Product Name: ETHYL (S)-2-HYDROXY-2-METHYLBENZENEPROPANOATE
• Synonyms: ETHYL (S)-2-HYDROXY-2-METHYLBENZENEPROPANOATE;(S)-2-Hydroxy-2-methyl-3-phenylpropionic acid ethyl ester
• CAS NO: 285130-47-4
• Molecular Formula: C₁₂H₁₆O₃
• Molecular Weight: 208.25
• Mol File: 285130-47-4.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ETHYL (S)-2-HYDROXY-2-METHYLBENZENEPROPANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: ETHYL (S)-2-HYDROXY-2-METHYLBENZENEPROPANOATE(285130-47-4)
• EPA Substance Registry System: ETHYL (S)-2-HYDROXY-2-METHYLBENZENEPROPANOATE(285130-47-4)

Safety Data

• Hazardous Substances Data: 285130-47-4(Hazardous Substances Data)

Upstream product

• 1115955-24-2 ethyl (2S,3R)-2,3-dihydroxy-2-methyl-3-phenylpropanoate 
• 103-79-7 1-phenyl-acetone 
• 64-17-5 ethanol 
• 219616-61-2 (S)-2-Hydroxy-2-methyl-4-phenylpropanenitrile 
• 92572-43-5 (2S,5S)-5-benzyl-2-(t-butyl)-5-methyl-1,3-dioxolan-4-one 

Downstream Products

• 1115955-03-7 ethyl (R)-2-azido-2-methyl-3-phenylpropanoate 
• 285130-53-2 (S)-benzyl hippuryl-α-methylphenyllactate 
• 285130-51-0 (S)-benzyl t-Boc-glycyl-α-methylphenyllactate 
• 285130-45-2 (S)-Hippuryl-alpha-methylphenyllactic acid 
• 285130-52-1 (S)-benzyl glycyl-α-methylphenyllactate 
• 285130-49-6 (S)-benzyl α-methylphenyllactate 
• 292617-57-3 (S)-3-Benzyloxy-5-benzyl-4-hydroxy-5-methyl-2(5H)-furanone 
• 292617-51-7 Ethyl (S)-2-benzyloxyacetoxy-2-methyl-3-phenylpropionate 
• 164333-77-1 (S)-α-methylphenyllactic acid 

Relevant articles and documents

Mitsunobu approach to the synthesis of optically active α,α-disubstituted amino acids

Chiral tertiary α-hydroxy esters of known stereochemical configuration were transformed to α-azido esters by Mitsunobu reaction with HN3. Optimization of this reaction was shown to proceed at room temperature with high chemical yield using 1,1-(azodicarbonyl)dipiperidine (ADDP) and trimethylphosphine (PMe3). Complete inversion of configuration was observed at the α-carbon. Several α,α- disubstituted amino acids were synthesized in high overall chemical yield and optical purity.

Hippuryl-α-methylphenylalanine and hippuryl-α-methylphenyllactic acid as substrates for carboxypeptidase A. Syntheses, kinetic evaluation and mechanistic implication

(R)- and (S)-Hippuryl-α-methylphenylalanine [(R)- and (S)-Hipp-α- MePhe] and (S)-hippuryl-α-methylphenyllactic acid [(S)-Hipp-α-MeOPhe] were synthesized and evaluated as substrates for carboxypeptidase A (CPA) in an effort to shed further light on the catalytic mechanism of the enzyme. The rate of CPA-catalyzed hydrolysis of (S)-Hipp-α-MePhe was reduced by 105-fold compared with that of (S)-Hipp-Phe, but the hydrolysis rate of (S)-Hipp-OPhe was lowered by only 6.8-fold by the introduction of a methyl group at the α- position. (R)-Hipp-α-MePhe failed to be hydrolyzed initially, then started to undergo hydrolysis in about 2 h at a much reduced rate. The results of present study may be envisioned on the basis of the proposition that while peptide substrate is hydrolyzed via a tetrahedral transition state formed by the attack of the zinc-bound water molecule at the peptide carbonyl carbon, ester hydrolysis takes the path that involves an anhydride intermediate generated by the attack of the carboxylate of Glu-270 at the ester carbonyl carbon. (C) 2000 Elsevier Science Ltd.