146912-63-2

Usage

Uses

Used in Pharmaceutical Industry:
2-(S)-HYDROXY-4-OXO-4-PHENYL-BUTYRIC ACID is used as a key intermediate in the synthesis of benzothiophenes, benzofurans, and indoles. These compounds are known for their potential therapeutic applications in the treatment of insulin resistance and hyperglycemia, which are common conditions associated with diabetes and metabolic disorders.
Used in Chemical Synthesis:
In the field of chemical synthesis, 2-(S)-HYDROXY-4-OXO-4-PHENYL-BUTYRIC ACID serves as a valuable starting material for the preparation of various complex organic molecules. Its unique structure allows for further functionalization and modification, making it a useful building block in the development of new pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Research and Development:
Due to its structural diversity and potential applications, 2-(S)-HYDROXY-4-OXO-4-PHENYL-BUTYRIC ACID is also utilized in research and development laboratories. Scientists and researchers use 2-(S)-HYDROXY-4-OXO-4-PHENYL-BUTYRIC ACID to study its chemical properties, reactivity, and potential interactions with other molecules, which can lead to the discovery of new drugs and materials.

Upstream product

• 59025-03-5 (S)-acetoxysuccinic anhydride 
• 71-43-2 benzene 
• 91497-49-3 4-phenyl-2-hydroxy-4-oxobutyric acid ethyl ester 
• 243658-52-8 (2S)-2-hydroxy-4-oxo-4-phenyl-butyric acid ethyl ester 

Downstream Products

• 125639-64-7 (S)-ethyl 2-hydroxy-4-phenylbutyrate 
• 90315-82-5 ethyl (R)-2-hydroxy-4-phenylbutyrate 
• 371255-35-5 ethyl (R)-2-azido-4-phenylbutanoate 
• 129277-07-2 ethyl (S)-2-methanesulfonyloxy-4-phenylbutanoate 
• 90940-54-8 (αR)-α-amino-benzenebutanoic acid ethyl ester hydrochloride 
• 124988-64-3 (S)-4-phenyl-1,2-butanediol 
• 587-63-3 7,8-dihydrokawain 
• 913258-21-6 (4S)-4-(2-phenylethyl)-1,3,2-dioxathiolane 2-oxide 
• 115016-95-0 (S)-2-hydroxy-4-phenylbutanoic acid 
• 13983-60-3 (3S,5R)-dihydro-3-hydroxy-5-phenylfuran-2(3H)-one 

Relevant academic research and scientific papers

Asymmetric synthesis of (S)-dihydrokavain from l-malic acid

A practical and efficient asymmetric synthesis of (S)-dihydrokavain from known ethyl (S)-2-hydroxy-4-phenylbutanoate which is, in turn, readily available from l-malic acid as a cheap chiral pool material is described using regioselective ring-opening of the 1,2-cyclic sulfate with lithium-3,3,3-triethoxypropiolate and subsequent HgO/H2SO4-mediated lactonization as the key steps. Its opposite enantiomer (R)-dihydrokavain was also synthesized from d-malic acid using the same sequences of reactions for the purpose of optical purity determination.

Lipase activity of Lecitase Ultra: characterization and applications in enantioselective reactions

The general properties of Lecitase Ultra, a phospholipase manufactured and marketed by Novozymes, Denmark, have been studied after purification by ultrafiltration. The enzyme has a molecular mass of 35 KD, pH-optimum of 8.5, and appears to possess a single active site which exhibits both the lipase and phospholipase activities that increase in the presence of Ca2+ and Mg2+ ions. The enzyme is inhibited by heavy metal ions and surfactants, and does not accept p-nitrophenyl acetate and glycerol triacetate. Substrates, such as glycerol tributyrate and p-nitrophenyl palmitate, esters of N-acetyl-α-amino acids and α-hydroxy acids are readily accepted. Amino acids with aliphatic residues, such as alanine, isoleucine, and methionine, are hydrolyzed with high enantioselectivity for the l-enantiomer (E >100), but amino acids with aromatic residues such as phenylalanine and phenylglycine, and esters of α-hydroxy acids are hydrolyzed with low enantioselectivity (E = 1-5). Immobilization of the enzyme in a gelatin matrix (gelozyme) leads to a marginal improvement in the enantioselectivity for these substrates. However, a dramatic improvement in enantioselectivity is observed for ethyl 2-hydroxy-4-oxo-4-phenylbutyrate (E value increases from 4.5 to 19.5 with S-selectivity). Similarly, glycidate esters, such as ethyl trans-(±)-3-phenyl glycidate and methyl trans-(±)-3-(4-methoxyphenyl) glycidate, are selectively hydrolyzed with a remarkable selectivity towards the (2S,3R)-enantiomer providing unreacted (2R,3S)-glycidate esters (ee >99%, conversion 52-55%) by the immobilized enzyme.

Enantio- and regiospecific reduction of ethyl 4-phenyl-2,4-dioxobutyrate with baker's yeast: Preparation of (R)-HPB ester

Ethyl 2,4-dioxo-4-phenylbutyrate obtained by condensation of acetophenone with diethyl oxalate is reduced enantio- and regiospecifically by baker's yeast in a diisopropyl ether/water two-phase system to give (-)-ethyl (R)-2-hydroxy-4-oxo-4-phenylbutyrate with an ee = 98% in 80% isolated yield. The hydroxyester was hydrogenated over Pd-C to obtain (-)-ethyl (R)-2-hydroxy-4-phenylbutyrate (HPB ester), an important intermediate for the synthesis of ACE inhibitors. Prolonged contact of the reduction product with baker's yeast produced 3-phenyl 3-oxo propanol in 90% yield.

A practical synthesis of ethyl (R)- and (S)-2-hydroxy-4-phenylbutanoate and D-homophenylalanine ethyl ester hydrochloride from L-malic acid

With the readily available L-malic acid as starting material, both enantiomers of ethyl 2-hydroxyl-4-phenylbutanoates and D-homophenylalanine ethyl ester hydrochloride were prepared conveniently in excellent optical purity and 64, 53 and 49% overall yield, respectively.

Synthesis of homochiral 2-hydroxy acids

A process for the production of a homochiral 2-hydroxy carboxylic acid or salt thereof corresponding to general formula (I), wherein R represents one of formulae (II), (III), (IV), (V), wherein R' represents straight- or branched-chain alkyl or phenyl opt

Stereoselective routes to chiral 2-hydroxy-4-oxo acids and substituted 2-hydroxybutyrolactones using lactate dehydrogenases

The enantioselective reduction 2,4-dioxo acids catalysed by lactate dehydrogenases provided access to 2-hydroxy-4-oxo acids of both S and R configuration. Subsequent diastereoselective chemical reduction affords 4-substituted 2-hydroxybutyrolactones.