86117-53-5

Usage

Uses

Used in Pharmaceutical Industry:
(R)-2-(4-MethylphenylsulfonaMido)-3-phenylpropanoic acid is utilized as a pharmaceutical intermediate, playing a vital role in the synthesis of various drugs and bioactive molecules. Its unique stereochemistry allows for targeted interactions with biological systems, enhancing the development of novel therapeutic agents.
Used in Medical Applications:
(R)-2-(4-MethylphenylsulfonaMido)-3-phenylpropanoicacid has been investigated for its potential anti-inflammatory and analgesic properties, making it a promising candidate for the treatment of pain and inflammation-related conditions. Its application in medical treatments could provide relief for patients suffering from a range of ailments.
Additionally, (R)-2-(4-MethylphenylsulfonaMido)-3-phenylpropanoic acid is employed in the management of various medical conditions, further demonstrating its versatility and potential impact on healthcare.

InChI:InChI=1S/C16H17NO4S/c1-12-7-9-14(10-8-12)22(20,21)17-15(16(18)19)11-13-5-3-2-4-6-13/h2-10,15,17H,11H2,1H3,(H,18,19)/t15-/m1/s1

Upstream product

• 673-06-3 D-(R)-phenylalanine 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 673-06-3 D-(R)-phenylalanine 
• 106-45-6 para-thiocresol 
• 629956-93-0 (2R,4S)-2-(4-fluoro-2-methyl)phenyl-4-hydroxypiperidine N-tosyl-D-phenylalanine salt 
• 1438047-59-6 C₂₄H₂₆N₂O₃S 

Relevant academic research and scientific papers

Palladium-Catalyzed Modular Synthesis of Substituted Piperazines and Related Nitrogen Heterocycles

We report here a novel method for the modular synthesis of highly substituted piperazines and related bis-nitrogen heterocycles via a palladium-catalyzed cyclization reaction. The process couples two of the carbons of a propargyl unit with various diamine components to provide nitrogen heterocycles in generally good to excellent yields and high regio- and stereochemical control. (Chemical Equation Presented).

Conversion of alanine and phenylalanine into weinreb amides by using different protecting groups

Efficient conversions of amino acids into Weinreb amides were achieved by treatment of amino acids with N,O-dimethylhydroxylamine hydrochloride in basic media. The amino group (-NH2) of amino acids were protected with p-toluene sulphonyl chlori

Oxazoline derivatives tagged with tosylated amino acids as recyclable organocatalysts for enantioselective allylation of aldehydes

A series of amino acid-based oxazoline compounds have been prepared and successfully applied to the enantioselective allylation reaction of aldehydes. The fine-tuning of the structure of the oxazolines led to (S,S)-4 as an efficient organocatalyst which gave homoallyl alcohols in good yield (up to 90%) and excellent ee (up to 99%) for a wide range of substrates including aromatic, hetero-aromatic and α,β-unsaturated aldehydes. The chiral organocatalyst was synthesized in three easy steps with an overall 88% yield and successfully recycled for up to three cycles. On the basis of the experimental observations and NMR studies, a probable mechanism was proposed for this reaction.

Synthetically amenable amide derivatives of tosylated-amino acids as organocatalysts for enantioselective allylation of aldehydes: Computational rationale for enantioselectivity

A phenylalanine derived chiral amide is developed that serves as an effective organocatalyst for the reaction of allyltrichlorosilane with aryl, hetero-aryl and α,β-unsaturated aldehydes to afford the desired homoallylic alcohols in good yield (up to 90%)

Oxazoline-based organocatalyst for enantioselective strecker reactions: A protocol for the synthesis of levamisole

A chiral oxazoline-based or-ganocatalyst has been found to efficiently catalyze asymmetric Strecker reactions of various aromatic and aliphatic N-benzhydrylimines with trime-thylsilyl cyanide (TMSCN) as a cyanide source at -20°C to give α-aminoni-triles in high yield (96%) with excellent chiral induction (up to 98% ee). DFT calculations have been performed to rationalize the enantioselective formation of the product with the organo-catalyst in these reactions. The organo-catalyst has been characterized by single-crystal X-ray diffraction analysis, as well as by other analytical methods. This protocol has been extended to the synthesis of the pharmaceutically important drug molecule levamisole in high yield and with high enantioselectivity.

Copper(II) triflate-catalyzed intramolecular hydroamination of homoallylic amino alcohols as an expedient route to trans-2,5-dihydro-1H-pyrroles and 1,2-dihydroquinolines

A new efficient synthetic route to trans-2,5-dihydro-1H-pyrroles and 1,2-dihydroquinolines that relies on copper(II) triflate-catalyzed intramolecular hydroamination of homoallylic amino alcohols under mild and operationally straightforward conditions is

Allylation of aldehydes and imines: Promoted by reuseable polymer-supported sulfonamide of N-glycine

A allylation of aldehydes and imines (generated in situ from aldehydes and amines) with allyltributyltin promoted by recoverable and reusable the polymer-supported sulfonamide of N-glycine has been developed. Good to high yields were obtained in various cases. Most of the SnBu3 residue can be recovered as Bu3SnCl. Highly stereoselective synthesis of N-Boc-(2S,3S)-3-hydroxy-2-phenylpiperidine 7 was achieved by using the P4a-mediated allylation of Boc-L-phenylglycinal as a key step.

Multi-step application of immobilized reagents and scavengers: A total synthesis of epothilone C

The total synthesis of the cytotoxic antitumour natural product epothilone C has provided a stage for the exploitation and further development of immobilized reagent methods. A stereoselective convergent synthetic strategy was applied, incorporating polymer-supported reagents, catalysts, scavengers and catch-and-release techniques to avoid frequent aqueous work-up and chromatographic purification.

Synthesis and structure of lower rim C-linked N-tosyl peptidocalix[4]arenes

Chiral p-tert-butylcalix[4]arenes functionalized at the lower rim with amino acid residues have been prepared. The 1H and 13C NMR spectra indicate that the macrocycles preferably adopt a cone conformation. Calix[4]arenes bearing amin

HIV protease inhibitors based on amino acid derivatives

A compound selected from the group consisting of a compound of formula I 1a compound of formula II 2and when the compound of formula I and II comprises an amino group pharmaceutically acceptable ammonium salts thereof, wherein R1, R2, Cx, n, R3, R4, R5, Y are as defined in the specification.