3966-32-3

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(-)-alpha-Methoxyphenylacetic acid is used as a synthetic intermediate for the development of various pharmaceutical compounds. Its primary application is in the synthesis of dopamine receptor agonists, which are essential for treating conditions related to dopamine deficiencies, such as Parkinson's disease.
Additionally, (R)-(-)-alpha-Methoxyphenylacetic acid is used to prepare hydroxytriamides, which are potent γ-secretase inhibitors. These inhibitors have potential applications in the treatment of Alzheimer's disease by modulating the production of amyloid-beta peptides, a key factor in the pathology of the disease.
Used in Chemical Research:
As a chiral derivatizing agent, (R)-(-)-alpha-Methoxyphenylacetic acid is employed in chemical research to help differentiate between enantiomers. This ability to convert enantiomers into diastereoisomers is vital for understanding the stereochemistry of molecules and their interactions with biological systems, which can lead to the development of more effective and selective drugs.

InChI:InChI=1/C9H10O3/c1-12-8(9(10)11)7-5-3-2-4-6-7/h2-6,8H,1H3,(H,10,11)/p-1/t8-/m1/s1

Upstream product

• 4755-72-0 Chloro-phenyl-acetic acid 
• 124-41-4 sodium methylate 
• 60686-79-5 (R)-2-bromo-2-phenylacetic acid 
• 611-71-2 (R)-Mandelic Acid 
• 77-78-1 dimethyl sulfate 
• 31528-00-4 (R)-2-Methoxy-2-phenylessigsaeure-4-nitrophenylester 
• 611-71-2 MANDELIC ACID 
• 538-86-3 benzyl methyl ether 
• 124-38-9 carbon dioxide 
• 17628-72-7 R-(-)-2-methoxy-2-phenyl ethanol 
• 20698-91-3 (R)-methyl mandelate 
• 7021-09-2 rac-methoxyphenylacetic acid 
• 86544-37-8 (S)-α-methoxyphenylacetaldehyde 
• 1260157-28-5 C₁₁H₁₁IO₃ 

Downstream Products

• 31528-00-4 (R)-2-Methoxy-2-phenylessigsaeure-4-nitrophenylester 
• 113581-35-4 (R)-O-Methylmandelic acid derivative of (-)-menthol 
• 133870-20-9 (R)-Methoxy-phenyl-acetic acid (1R,2S)-2-hydroxy-2-vinyl-cyclopentyl ester 
• 123642-99-9 (R)-O-Methylmandelic acid derivative of (2R,3R,4S,5R)-3-Hydroxy-2-methoxy-8-methyl-5-tetradecanoylnon-6-ene 1,4-lactone 
• 124126-42-7 2-((R)-2-Methoxy-2-phenyl-acetoxy)-3-propenylidene-decanoic acid methyl ester 
• 131352-38-0 (4R,5R,2E,6E)-4-(methoxymethoxy)-2,6-undecadien-5-yl (R)-O-methylmandelate 
• 131433-69-7 (4R,5R,2E)-4-(methoxymethoxy)-2-undecen-5-yl (R)-O-methylmandelate 
• 131433-70-0 (4R,5R,2E)-4-(methoxymethoxy)-2-undecen-6-yn-5-yl (R)-O-methylmandelate 
• 131352-39-1 (1R,2R,3E)-1-cyclohexyl-2-(methoxymethoxy)-3-penten-1-yl (R)-O-methylmandelate 
• 131352-42-6 (1R,2R,3E)-1-phenyl-2-(methoxymethoxy)-3-penten-1-yl (R)-O-methylmandelate 
• 124126-30-3 2-((R)-2-Methoxy-2-phenyl-acetoxy)-3-propenylidene-heptanoic acid methyl ester 
• 124152-72-3 (R)-Methoxy-phenyl-acetic acid 2-propenylidene-hexyl ester 
• 124126-41-6 (R)-Methoxy-phenyl-acetic acid 2-propenylidene-nonyl ester 
• 133870-22-1 (R)-Methoxy-phenyl-acetic acid (3aR,7aR)-4-oxo-octahydro-benzofuran-2-ylmethyl ester 

Relevant academic research and scientific papers

C3-Symmetric Tricyclo[2.2.1.02,6]heptane-3,5,7-triol

A straightforward access to a hitherto unknown C3-symmetric tricyclic triol both in racemic and enantiopure forms has been developed. Treatment of 7-tert-butoxynorbornadiene with peroxycarboxylic acids provided mixtures of C1- and C3-symmetric 3,5,7-triacyloxynortricyclenes via transannular π-cyclization and replacement of the tert-butoxy group. By refluxing in formic acid, the C1-symmetric esters were converted to the C3-symmetric formate. Hydrolysis gave diastereoisomeric triols, which were separated by recrystallization. Enantiomer resolution via diastereoisomeric tri(O-methylmandelates) delivered the target triols on a gram scale. The pure enantiomers are useful as core units of dopants for liquid crystals.

(R)- N - [5 - (2 - methoxy - 2 - phenyl-acetyl) - 1, 4, 5, 6 - tetrahydro-pyrrolo [3, 4 - c] pyrazole - 3 - yl] - 4 - (4 - methyl piperazine - 1 - yl) benzamide synthesis method

The invention belongs to the technical field of medicine and relates to a preparation method for PHA739358(Danusertib), i.e., (R)-N-[5-(2-methoxy-2-phenylacetyl)-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole-3-yl]-4-(4-methyl piperazine-1-yl)benzamide. According to the invention, altogether four reaction routes are designed, simple and easily available glycine is used as a raw material, reactions like addition, esterification, amino protection and cyclization are carried out so as to prepare (R)-N-[5-(2-methoxy-2-phenylacetyl)-1,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole-3-yl]-4-(4-methyl piperazine-1-yl)benzamide, yield of the route 1, 2 and 4 is more than 25%, respectively, and yield of the route 3 is more than 20%. The preparation method has the advantages of a few reaction steps, simple and convenient post-treatment operation, little time consumption, high yield and low total cost. Thus, a novel method is provided for preparation of the antitumor drug PHA739358.

Effect of the concentration of organic modifier in an aqueous-ethanol mobile phase on the chromatographic retention and thermodynamic characteristics of the adsorption of enantiomers of α-phenylcarboxylic acids on silica gel with immobilized eremomycin antibiotic

Regularities of the chromatographic retention and thermodynamics of the adsorption of enantiomers of α-phenylcarboxylic acids on a chiral stationary phase with immobilized macrocyclic antibiotic eremomycin under conditions of reversed-phase liquid chromatography with aqueous-ethanol mobile phases are studied. Relationships between the retention characteristics of the acids, the enantioselectivity of their separation, and the concentration of organic modifier in the mobile phase are found. It is shown that the sterical structure of substituents on the chiral atoms of the acids affect the mechanism of retention. The compensation effect in the studied systems is considered.

Enantioseparation of typical pesticides using cellulose carbamate stationary phases by capillary liquid chromatography

Cellulose-tris(3,5-dimethylphenylcarbamate) was initially synthesized as the chiral selector, then stable coated and bonded chiral stationary phases were prepared, respectively, using aminopropyl-functionalized silica gel as the support media. The prepared stationary phases were used for micro-column chiral separation by self-installed capillary high performance liquid chromatography system. Eighteen kind of chiral compounds including some typical pesticides were tested on both prepared chiral stationary phases and different chromatographic parameters such as resolution and retention time were comparatively investigated.

High-performance liquid chromatography separation of enantiomers of mandelic acid and its analogs on a chiral stationary phase

The enantiomers of mandelic acid and its analogs have been chromatographically separated on a chiral stationary phase (CSP) derived from 4-(3,5-dinitrobenzamido) tetrahydrophenanthrene. The rationale of separations of these compounds is discussed with respect to the method development for determining enantiomeric purity and possibility of obtaining enantiomerically pure materials by high-pressure liquid chromatography. The relationship of analyte structure to the extent of enantiomeric separation has been examined and separation factors (a) are presented for various groups of structurally related compounds. Chiral recognition models have been suggested to account for the observed separations. These models provide mechanistic insights into the chiral recognition process.

Kinetic resolution of (R,S)-pyrazolides containing substituents in the leaving pyrazole for increased lipase enantioselectivity

With hydrolysis of (R,S)-azolides in water-saturated methyl tert-butyl ether (MTBE) via Candida antarctica lipase B (CALB) as the model system, (R,S)-pyrazolides containing a leaving 3-, 4- or 3,4-substituted-pyrazole moiety are selected as the best substrates for preparing various optically pure carboxylic acids containing an α-chiral center. Great improvements of enzyme activity for the (R)-enantiomers with excellent enantioselectivity (VR/VS > 100) are obtainable, if (R,S)-pyrazolides containing a leaving 3- or 3,4-substituted-pyrazole moiety are employed for the hydrolysis or alcoholysis by methanol in anhydrous MTBE. A detailed kinetic analysis for (R,S)-N-2-phenylpropionylpyrazoles indicates that a bulky 3-substituent such as 3-(3-bromophenyl) or 3-(2-pyridyl) in the leaving pyrazole moiety has profound effects on decreasing the nucleophilic attack and proton transfer of catalytic serine for the slow-reacting enantiomer in anhydrous MTBE, as well as that and substrate affinity for both enantiomers in water-saturated MTBE. The resolution platform is also successfully applied to the hydrolysis of (R,S)-pyrazolides in water-saturated cyclohexane via Candida rugosa lipase (Lipase MY) having opposite enantioselectivity to CALB.

Homobenzotetramisole-catalyzed kinetic resolution of α-Aryl-, α-Aryloxy-, and α-Arylthioalkanoic acids

Effective kinetic resolutions of α-aryl-, αaryloxy-, and α-arylthioalkanoic acids have been achieved via in situ generation of their symmetrical anhydrides and enantioselective alcoholysis in the presence of homobenzotetramisole (HBTM) 3.

Enantiomerically pure α-methoxyaryl acetaldehydes as versatile precursors: a facile chemo-enzymatic methodology for their preparation

A facile and efficient synthesis of optically active α-methoxyaryl acetic acids (up to 95% ee), α-methoxyaryl ethanols (up to 93% ee) and α-methoxyaryl acetonitriles (up to 93% ee) was achieved via Arthrobacter sp. lipase-catalyzed kinetic resolution of masked aldehydes as the key synthons, that is, α-hydroxyaryl acetaldehyde acetals.

Parallel kinetic resolution of 2-methoxy and 2-phenoxy-substituted carboxylic acids using a combination of quasi-enantiomeric oxazolidinones

2-Methoxy-2-phenyl acetic acid and 2-phenoxy-2-phenylpropionic acid were resolved by the parallel kinetic resolution of their corresponding pentafluorophenyl active ester using a quasi-enantiomeric combination of lithiated oxazolidinones.