147383-72-0

Usage

Uses

Used in Pharmaceutical Industry:
Benzenepropanoic acid, α-(hydroxyMethyl)-, (S)is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique structure allows for the development of novel drugs with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of organic chemistry, Benzenepropanoic acid, α-(hydroxyMethyl)-, (S)serves as a valuable building block for the synthesis of complex organic molecules. Its reactivity and chirality make it a versatile component in the creation of new chemical entities.
Used in Synthesis of N-Acyl-N-hydroxy-β-amino acid derivatives:
Benzenepropanoic acid, α-(hydroxyMethyl)-, (S)is used as a reagent in the synthesis of N-Acyl-N-hydroxy-β-amino acid derivatives. These derivatives have the potential to inhibit the stereochemistry of hydroxamate inhibitors for thermolysin, an enzyme involved in various biological processes. This application highlights the compound's utility in the development of enzyme inhibitors, which can be crucial in understanding and treating certain diseases.

Upstream product

• 123542-72-3 (S)-2-benzyl-3-hydroxypropanoic acid methyl ester 
• 85677-12-9 2-benzyl-3-hydroxypropionic acid methyl ester 
• 462118-49-6 (+)-(S)-3-Benzyl-2-oxetanone 
• 2601-10-7 2‐benzyl‐3‐hydroxypropanenitrile 
• 1134366-48-5 (S)-2-benzyl-N,N-diphenylmalonamic acid 
• 50-00-0 formaldehyd 
• 1012-05-1 D,L-homophenylalanine 
• 501-52-0 3-Phenylpropionic acid 
• 220041-91-8 (R)-4-phenyl-N-(3'-phenylpropanoyl)-1,3-oxazolidin-2-one 
• 110270-49-0 (R)-3-acetoxy-2-benzyl-1-propanol 
• 49769-78-0 2-benzyl-malonic acid dimethyl ester 
• 2612-30-8 2-benzyl-1,3-propanediol 
• 6811-98-9 (RS)-2-hydroxymethyl-3-phenylpropionic acid 
• 187610-68-0 (+/-)-α-<(acetoxy)methyl>benzenepropanoic acid 

Downstream Products

• 116111-79-6 (R)-3-(acetylthio)-2-benzylpropanoic acid 
• 124815-67-4 (S)-2-acetylthiomethyl-3-phenylpropanoic acid 
• 238420-21-8 N-(S-2-hydroxymethyl-1-oxo-3-phenylpropyl)-glycine benzyl ester 
• 123542-72-3 (S)-2-benzyl-3-hydroxypropanoic acid methyl ester 
• 1314751-83-1 ethyl N-[(2S)-2-benzyl-3-hydroxypropanoyl]glycinate 
• 1314751-88-6 ethyl 2-((S)-2-benzyl-3-((3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl)propanamido)acetate hydrochloride 
• 1352995-69-7 ethyl N-[(2S)-2-benzyl-3-{[(4-bromophenyl)sulfonyl]oxy}propanoyl]glycinate 
• 156053-89-3 Entereg 
• 81110-73-8 (R)-benzyl N-[3-(acetylthio)-2-benzylpropanoyl]glycinate 
• 81110-73-8 N-(S-2-acetylthiomethyl-1-oxo-3-phenylpropyl)-glycine benzyl ester 
• 462118-49-6 (+)-(S)-3-Benzyl-2-oxetanone 

Relevant academic research and scientific papers

Chemoenzymatic Production of Enantiocomplementary 2-Substituted 3-Hydroxycarboxylic Acids from l-α-Amino Acids

A two-enzyme cascade reaction plus in situ oxidative decarboxylation for the transformation of readily available canonical and non-canonical l-α-amino acids into 2-substituted 3-hydroxycarboxylic acid derivatives is described. The biocatalytic cascade consisted of an oxidative deamination of l-α-amino acids by an l-α-amino acid deaminase from Cosenzaea myxofaciens, rendering 2-oxoacid intermediates, with an ensuing aldol addition reaction to formaldehyde, catalyzed by metal-dependent (R)- or (S)-selective carboligases namely 2-oxo-3-deoxy-l-rhamnonate aldolase (YfaU) and ketopantoate hydroxymethyltransferase (KPHMT), respectively, furnishing 3-substituted 4-hydroxy-2-oxoacids. The overall substrate conversion was optimized by balancing biocatalyst loading and amino acid and formaldehyde concentrations, yielding 36–98% aldol adduct formation and 91–98% ee for each enantiomer. Subsequent in situ follow-up chemistry via hydrogen peroxide-driven oxidative decarboxylation afforded the corresponding 2-substituted 3-hydroxycarboxylic acid derivatives. (Figure presented.).

IMPROVED PROCESS FOR THE PREPARATION OF [[2(S)-[[4(R)-(3-HYDROXYPHENYL)-3(R),4-DIMETHYL-1-PIPERIDINYL]METHYL]-1-OXO-3-PHENYLPROPYL]AMINO]ACETIC ACID DIHYDRATE

The present invention relates to an improved process for the preparation of [[2(S)-[[4(R)-(3-hydroxyphenyl)-3(R),4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-phenylpropyl]amino]acetic acid dihydrate, represented by the following structural formula (I).

The highly enantioselective phase-transfer catalytic mono-alkylation of malonamic esters

The phase-transfer catalytic alkylation of N,N-dialkylmalonamic tert-butyl esters in the presence of 1 mol% of (S,S)-3,4,5-trifluorophenyl-NAS bromide afforded highly enantioselective (S)-mono-α-alkylated products (up to 96% ee), which could be readily converted into versatile chiral building blocks without loss of chirality. The Royal Society of Chemistry.

Nitrile biotransformations for the synthesis of enantiomerically enriched β2-, and β3-hydroxy and -alkoxy acids and amides, a dramatic O-substituent effect of the substrates on enantioselectivity

Rhodococcus erythropolis AJ270, a nitrile hydratase/amidase-containing microbial whole cell catalyst, is able to catalyze the hydrolysis of a number of β-hydroxy and β-alkoxy nitriles under very mild conditions. Both the efficiency and enantioselectivity of the biocatalysis, however, were strongly dependent upon the structures of both nitrile and amide substrates. When biotransformations of racemic 3-hydroxy-3-phenylpropionitrile and 2-hydroxymethyl-3-phenylpropionitrile gave low enantioselectivity, their O-methylated isomers underwent highly efficient and enantioselective biocatalytic reactions to afford highly enantioenriched β2- and β3-hydroxy amide and acid derivatives in excellent yield. The study has provided an example of simple and very convenient substrate engineering method to increase the enantioselectivity of the biocatalytic reaction.

Method for producing optically active phenylpropionic acid derivative

Optically active N-(S-2-acetylthiomethyl-1-oxo-3-phenylpropyl)-glycine benzyl ester useful as an enkephalin inhibitory agent or ACE inhibitory agent can be produced at low cost in an industrial manner, by a method comprising subjecting optically active 2-hydroxymethyl-3-phenylpropionic acid and glycine benzyl ester to condensation to subsequently convert the hydroxyl group into an elimination group, and substituting the elimination group with an acetylthio group.

Cleavage of β-lactone ring by serine protease. Mechanistic implications

Both enantiomers of 3-benzyl-2-oxetanone (1) were found to be slowly hydrolyzed substrates of α-chymotrypsin having kcat values of 0.134±0.008 and 0.105±0.004 min-1 for (R)-1 and (S)-1, respectively, revealing that α-CT is virtually unable to differentiate the enantiomers in the hydrolysis of 1. The initial step to form the acyl-enzyme intermediate by the attack of Ser-195 hydroxyl on the β-lactone ring at the 2-position in the hydrolysis reaction may not be enzymatically driven, but the relief of high ring strain energy of β-lactone may constitute a major driving force. The deacylation step is also attenuated, which is possibly due to the hydrogen bond that would be formed between the imidazole nitrogen of His-57 and the hydroxyl group generated during the acylation in the case of (R)-1, but in the α-CT catalyzed hydrolysis of (S)-1 the imidazole nitrogen may form a hydrogen bond with the ester carbonyl oxygen.

Sulfonic acid ester derivatives, method for production thereof and use thereof

Novel and useful optical active 2-aralkyl-3-sulfonyloxy-1-propanol and 2-aralkyl-3-sulfonyloxypropionic acid are provided by using an optical active 2-aralkyl-3-acyloxy-1-propanol as a starting material. Furthermore, an optical active 2-aralkyl-3-thiopropionic acid, which is an important intermediate of enkephalinase inhibitor, is provided. According to the present invention, industrially useful optical active sulfonic acid ester derivatives can be provided.

New asymmetric synthesis of dexecadotril and ecadotril starting from a single precursor

We describe herein a method providing access to both enantiomers of 3-acetylthio-2-benzylpropionic acid via enzymatic desymmetrization of 2-benzyl-1,3-propanediol. These compounds are respectively the starting materials for the synthesis of ecadotril, and dexecadotril, which are powerful inhibitors of NEP (EC 3.4.24.11) and have been developed as therapeutic agents.

PROCESS FOR THE ASYMMETRIC SYNTHESIS OF S-ACYL DERIVATIVES OF 2-MERCAPTOMETHYL -3- PHENYL PROPANOIC ACID, APPLICATION TO THE SYNTHESIS OF N-(MERCAPTOACYL) AMINO ACID DERIVATIVES

Process for the asymmetric synthesis of S-acyl derivatives of 2-mercaptomethyl-3-phenylpropanoic acid of formula (I): characterized in that it comprises the steps consisting in:a) preparing the diol (VI) by reduction of a malonic ester (V) in the presence of a hydride; b) preparing the monoacetates (VII R) or (VII S) respectively; c) subjecting these monoacetates to an oxidation in order to form the acids (IX S) or (IX R);d) saponifying the compounds (IX S) or (IX R) in order to form the hydroxy acids (X S) or (X R);e) thioacylating the hydroxy acids (X S) or (X R) with a mercapto acid R. sub.1 SH (XI), according to a Mitsunobu-type reaction, in order to lead to the desired acids (I R) (I S) respectively and application to the synthesis of N-(mercaptoacyl)amino acid derivatives (II). STR1