3966-30-1

Usage

Uses

Used in Pharmaceutical Industry:
(R)-(-)-2-HYDROXY-2-PHENYLPROPIONIC ACID is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique stereochemistry and functional groups make it a versatile building block for creating new drugs with specific biological activities.
Used in Asymmetric Synthesis:
(R)-(-)-2-HYDROXY-2-PHENYLPROPIONIC ACID is used as a chiral building block in asymmetric synthesis, which is a branch of chemistry that focuses on the creation of molecules with specific three-dimensional structures. (R)-(-)-2-HYDROXY-2-PHENYLPROPIONIC ACID is particularly useful in the stereospecific synthesis of other chiral molecules, such as (R)and (S)-2-cyclohexyl-2-hydroxy-2-phenylacetic acid.
Used in Research and Development:
(R)-(-)-2-HYDROXY-2-PHENYLPROPIONIC ACID is also used in research and development for studying the configurational relationships between different chiral molecules. Understanding these relationships is crucial for the development of new drugs and materials with specific properties and applications.

InChI:InChI=1/C9H10O3/c1-9(12,8(10)11)7-5-3-2-4-6-7/h2-6,12H,1H3,(H,10,11)/t9-/m1/s1

Upstream product

• 4023-95-4 (R)-2-hydroxy-2-phenyl-propionamidine; hydrochloride 
• 81036-98-8 (S)-2-tert-Butyl-5-methyl-5-phenyl-[1,3]dioxolan-4-one 
• 117606-77-6 (S)-2-Methyl-3-oxo-2-phenyl-butyric acid methyl ester 
• 5704-66-5 pyruvoyl chloride 
• 13448-80-1 methyl R-(-)-atrolactate 
• 110457-29-9 (S)-2-hydroxymethyl-N-((R)-2-hydroxy-2-phenyl)propanoylpyrrolidine 
• 917-64-6 methyl magnesium iodide 
• 6191-36-2 (R)-Atrolactinsaeureamid 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 515-30-0 2-phenyllactic acid 
• 682352-12-1 (1S,2R,3S,5R,1'S,2'R)-6,6-dimethyl-3-(1'-ethoxy-2'-phenyl-2'-hydroxy-1'-propylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane 
• 6175-45-7 2,2-diethoxyacetophenone 
• 17199-29-0 (S)-Mandelic acid 
• 25726-04-9 phenylglyoxylyl chloride 

Downstream Products

• 13448-80-1 methyl R-(-)-atrolactate 
• 70908-68-8 R-Hexahydrolactinsaeure 
• 2406-23-7 (R)-ethyl 2-hydroxy-2-phenylpropanoate 
• 17325-55-2 (+/-)-2-chloro-2-phenyl-propionic acid 
• 2406-22-6 (R)-1-phenyl-1,2-ethanediol 
• 439117-51-8 [4-Chloro-2-({[(S)-1-((R)-2-hydroxy-2-phenyl-propionyl)-pyrrolidine-2-carbonyl]-amino}-methyl)-benzyl]-carbamic acid tert-butyl ester 
• 859723-78-7 (R)-2-Hydroxy-2-phenyl-propionic acid 8-bromo-octyl ester 
• 1097209-29-4 C₂₇H₂₈Cl₂N₂O₄ 
• 648424-77-5 benzyl (R)-(+)-2-hydroxy-2-phenylpropanoate 
• 1219630-42-8 C₄₂H₄₂N₄O₆ 

Relevant academic research and scientific papers

Highly Diastereoselective Addition of Organometallics to Novel Chiral α-Ketoamides of (S)-2-Methoxymethylindoline

The stereocontrolled nucleophilic addition of organometallics to novel chiral α-ketoamides which were synthesized from (S)-2-methoxymethylindoline as a chiral auxiliary was carried out to obtain α-hydroxyamides with extremely high diastereoselectivities (up to dr 99:1).

La1?xSrxFeO3 perovskite electrocatalysts for asymmetric electrocarboxylation of acetophenone with CO2

The use of La1?xSrxFeO3 (x= 0, 0.1, 0.2, 0.3, 0.4 and 0.5) cathodes in asymmetric electrocarboxylation of acetophenone with CO2 induced by chiral auxiliary CoII-(salen) was investigated for the first time. Optically active 2-hydroxy-2-phenylpropionic acid with 94% enantiomeric excess and 68% yield were obtained. The superior asymmetric electrocarboxylation performance may derive from the Fe4+ species and the increased lattice oxygen concentration on the surface of La0.7Sr0.3FeO3 (LSF-0.3) induced by Sr-doping, together with an accelerated electron transfer and an increased electrochemically active surface area. Here, perovskite oxide catalyst has an acid function, which is supplied by Fe4+ ions, can participate in the reaction by coordinating with acetophenone. Moreover, the LSF-0.3 has considerable stability and reusability. By cyclic voltammograms and contrast experiments, a mechanism was proposed for the asymmetric electrocarboxylation reaction.

Solvent-induced chirality switching in the enantioseparation of regioisomeric hydroxyphenylpropionic acids via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol

The enantioseparation of three hydroxyphenylpropionic acid isomers via diastereomeric salt formation with (1R,2S)-2-amino-1,2-diphenylethanol has been demonstrated. The racemates of all three acid isomers were successfully separated with high efficiency (0.56–0.84) after single crystallization. For 2-hydroxy-3-phenylpropionic acid 4, the configuration of the less-soluble salt was controlled by the crystallization solvent: the (R)-4 salt was crystallized from water, while 2-propanol afforded the (S)-4 salt. The chiral recognition mechanism of the three acids was discussed based on the crystal structures of the diastereomeric salts.

Entrapment of a chiral cobalt complex within silver: A novel heterogeneous catalyst for asymmetric carboxylation of benzyl bromides with CO2

A novel way to accommodate heterogeneous catalysis, CO2 fixation and asymmetric synthesis on one catalyst is reported. The [Co]@Ag composite was prepared for the first time and used for asymmetric carboxylation of benzyl bromides with CO2. All the procedures were performed under mild conditions. Moreover, the [Co]@Ag composite has terrific stability and reusability.

Development of a new family of chiral auxiliaries

A new family of chiral auxiliaries designed on a conformationally restricted version of (-)-8-phenylmenthol has been developed. Both enantiomers are available from an inexpensive synthesis conducted on multigram scale. A first application has showed compa

Absolute configuration and enantiomeric composition of partially resolved mandelic,atrolactic and lactic acids by 1H NMR of their (S)-2-methylbutyl esters

The mandelic,atrolactic and lactic acid esters of the (S)-2-methyl-1- butanol were examined as diastereomeric derivatives for the stereochemical analysis of the mentioned acids by 1H nuclear magnetic resonance (NMR) at 300 MHz. The diastereomer

Evaluation of dalbavancin as chiral selector for HPLC and comparison with teicoplanin-based chiral stationary phases

Dalbavancin is a new compound of the macrocyclic glycopeptide family. It was covalently linked to 5 lm silica particles using two different binding chemistries. Approximately 250 racemates including (a) heterocyclic compounds, (b) chiral acids, (c) chiral amines, (d) chiral alcohols, (e) chiral sulfoxides and sulfilimines, (f) amino acids and amino acid derivatives, and (g) other chiral compounds were tested on the two new chiral stationary phases (CSPs) using three different mobile phases. As dalbavancin is structurally related to teicoplanin, the same set of chiral compounds was screened on two commercially available teicoplanin CSPs for comparison. The dalbavancin CSPs were able to separate some enantiomers that were not separated by the teicoplanin CSPs and also showed improved separations for many racemates. However, there were other compounds only separated or better separated on teicoplanin CSPs. Therefore, the dalbavancin CSPs are complementary to the teicoplanin CSPs.

B-allenyl- and B-(γ-trimethylsilylpropargyl)-10-phenyl-9- borabicyclo[3.3.2]decanes: Asymmetric synthesis of propargyl and α-allenyl 3°-carbinols from ketones

Simple and efficient Grignard procedures are reported for the syntheses of B-allenyl-10-(phenyl)-9-borabicyclo[3.3.2]decane (1) and its B-(γ-trimethylsilylpropargyl) counterpart (2) in both enantiomeric forms. Both add selectively to ketones, providing propargyl- and α-silylallenyl 3°-carbinols, respectively (i.e., 6 (61-93% ee) and 9 (64-98% ee)). The air-stable boron byproduct is efficiently recovered and recycled back to either 1 or 2. The ozonolysis and bromination of 9 provide nonracemic α-hydroxy acids and γ-bromopropynyl carbinols, respectively.

Enantioselective synthesis of either enantiomer of α-alkyl-α- hydroxy-α-phenylacetic acids using chiral auxiliaries

The enantioselective synthesis of either enantiomer of α-alkyl- α-hydroxy-α-phenylacetic acids was achieved by using 2-acyloxathianes 1a-c and the mixed acyl-S,O-acetals 7 and 8 as chiral auxiliaries, which can straightforwardly be prepared from (1R)-(-)-myrtenal. This procedure allowed the preparation of the title compounds in >95% enantiomeric excess (ee).

Stereoselective synthesis of α-alkyl-α-hydroxylphenylacetic acid. Part (I): Asymmetric alkylation of (S)-mandelic acid

An effective asymmetric synthesis of α-alkyl-α-hydroxyl phenyl acetic acid using benzaldehyde as steric hindrance agent has been accomplished by utilising the readily available and inexpensive chiral starting material, (S)-mandelic acid. The ee was determined by 1H NMR with Eu(hfc) 3 as shift reagent.