86555-45-5

Usage

Uses

Used in Pharmaceutical Industry:
(S)-dimethyl 2-benzamidosuccinate is used as a chiral ligand in asymmetric synthesis for the development of enantiomerically pure compounds, which are essential in the pharmaceutical industry to ensure the desired therapeutic effects and minimize side effects.
(S)-dimethyl 2-benzamidosuccinate is used as a building block in the synthesis of various bioactive compounds, contributing to the discovery of new drugs with potential therapeutic applications.
Used in Drug Discovery and Development:
(S)-dimethyl 2-benzamidosuccinate is used as an enzyme inhibitor targeting enzymes involved in various biological processes, making it a promising candidate for the development of drugs to treat specific diseases and conditions.
Used in Chemical Industry:
(S)-dimethyl 2-benzamidosuccinate is used in the chemical industry for the synthesis of various compounds and materials, leveraging its unique structural and stereochemical properties.

Upstream product

• 55-21-0 benzamide 
• 762-42-5 dimethyl acetylenedicarboxylate 
• 32213-95-9 dimethyl L-aspartate hydrochloride 
• 98-88-4 benzoyl chloride 
• 6384-18-5 L-Aspartic acid dimethyl ester 
• 67-56-1 methanol 
• 171898-36-5 methyl (S)-N-benzoyl-3-(1,4-cyclohexadien-1-yl)alaninate 
• 2177-62-0 β-methyl L-aspartate 
• 39741-26-9 N-benzoyl-L-aspartic acid β-methyl ester 
• 60272-64-2 2-phenyl-4-methoxycarbonylmethyl-5-oxo-4,5-dihydro-1,3-oxazole 
• 186581-53-3 diazomethane 
• 82933-21-9 N-benzoyl-L-aspartic acid α-methyl ester 
• 127-09-3 sodium acetate 
• 32213-95-9 DL-aspartic acid dimethyl ester hydrochloride 

Downstream Products

• 252580-08-8 (4S,5S)-2-phenyloxazoline-4,5-dicarboxylic acid dimethyl ester 
• 296766-73-9 (1S)-N-[3-hydroxy-1-(hydroxymethyl)propyl]benzamide 
• 327615-67-8 (S)-2-(2-phenyl-4,5-dihydrooxazol-4-yl)ethyl 4-methylbenzenesulfonate 
• 369657-14-7 (S)-2-phenyl-4-(2-iodoethyl)oxazoline 
• 369657-21-6 1-((((S)-4',5'-dihydro-2'-phenyl-4'-oxazolyl)ethyl)-3-(2,6)-diisopropylphenyl)imidazolium iodide 
• 144946-64-5 2-phenyl-oxazole-4,5-dicarboxylic acid dimethyl ester 

Relevant academic research and scientific papers

Microwave-Assisted Ruthenium-Catalysed ortho-C?H Functionalization of N-Benzoyl α-Amino Ester Derivatives

A microwave-assisted highly efficient intermolecular C?H functionalization sequence has been developed to access substituted isoquinolones using α-amino acid esters as a directing group. This methodology enables a wide range of N-benzoyl α-amino ester derivatives to react via a Ru-catalysed C?H bond activation sequence, to form isoquinolones with moderate to excellent yields. As an additional advantage, our strategy proved to be widely applicable and also enabled the reaction of alkenes to provide access to alkenylated benzamides. The methodology was also extended towards the synthesis of isoquinoline alkaloids derivatives viz. oxyavicine and a dipeptide. The developed protocol is simple and cheap, avoids tedious workup procedures and works efficiently under MW irradiation. (Figure presented.).

Design and optimization of aspartate N-acetyltransferase inhibitors for the potential treatment of Canavan disease

Canavan disease is a fatal neurological disorder caused by defects in the metabolism of N-acetyl-L-aspartate (NAA). Recent work has shown that the devastating symptoms of this disorder are correlated with the elevated levels of NAA observed in these patients, caused as a consequence of the inability of mutated forms of aspartoacylase to adequately catalyze its breakdown. The membrane-associated enzyme responsible for the synthesis of NAA, aspartate N-acetyltransferase (ANAT), has recently been purified and examined (Wang et al., Prot Expr Purif. 2016;119:11). With the availability, for the first time, of a stable and soluble form of ANAT we can now report the identification of initial inhibitors against this biosynthetic enzyme, obtained from the screening of several focused compound libraries. Two core structures of these moderate binding compounds have subsequently been optimized, with the most potent inhibitors in these series possessing sub-micromolar inhibition constants (Kivalues) against ANAT. Slowing the production of NAA via the inhibition of ANAT will lower the elevated levels of this metabolite and can potentially serve as a treatment option to moderate the symptoms of Canavan disease.

POTENT INHIBITORS OF ASPARTATE N-ACETYL-TRANSFERASE FOR THE TREATMENT OF CANAVAN DISEASE

Compounds, compositions, and methods for the treatment of Canavan disease are described.

SUBSTITUTED BRIDGED UREA ANALOGS AS SIRTUIN MODULATORS

The present invention relates to novel substituted bridged urea compounds, corresponding related analogs, pharmaceutical compositions and methods of use thereof. Sirtuin-modulating compounds of the present invention may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders, which include, but are not limited to, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. The present invention also related to compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

SUBSTITUTED BRIDGED UREA ANALOGS AS SIRTUIN MODULATORS

Provided herein are novel substituted bridged urea and related analogs and methods of use thereof. The sirtuin-modulating compounds may be used for increasing the lifespan of a cell, and treating and/or preventing a wide variety of diseases and disorders including, for example, diseases or disorders related to aging or stress, diabetes, obesity, neurodegenerative diseases, cardiovascular disease, blood clotting disorders, inflammation, cancer, and/or flushing as well as diseases or disorders that would benefit from increased mitochondrial activity. Also provided are compositions comprising a sirtuin-modulating compound in combination with another therapeutic agent.

Peptide-catalyzed conversion of racemic oxazol-5(4 H)-ones into enantiomerically enriched α-amino acid derivatives

We report the development and optimization of a tetrapeptide that catalyzes the methanolytic dynamic kinetic resolution of oxazol-5(4H)-ones (azlactones) with high levels of enantioinduction. Oxazolones possessing benzylic-type substituents were found to perform better than others, providing methyl ester products in 88:12 to 98:2 er. The mechanism of this peptide-catalyzed process was investigated through truncation studies and competition experiments. High-field NOESY analysis was performed to elucidate the solution-phase structure of the peptide, and we present a plausible model for catalysis.

Expeditious novel routes to enantiopure 3-amino tetrahydrofuran hydrochloride

The synthesis of chemically and enantiomerically pure (S)-3-amino tetrahydrofuran hydrochloride starting from the natural amino acids, l-aspartic acid or l-methionine is described. The process involves no chromatography and can be easily carried out on a large scale. The enantiopurity of the final product was established by NMR and chiral HPLC methods.

Stereo-controlled asymmetric bioreduction of α,β-dehydroamino acid derivatives

α,β-Dehydroamino acid derivatives proved to be a novel substrate class for ene-reductases from the 'old yellow enzyme' (OYE) family. Whereas N-acylamino substituents were tolerated in the α-position, β-analogues were generally unreactive. For aspartic aci

Improved catalysts for the iridium-catalyzed asymmetric isomerization of primary allylic alcohols based on charton analysis

An improved generation of chiral cationic iridium catalysts for the asymmetric isomerization of primary allylic alcohols is disclosed. The design of these air-stable complexes relied on the preliminary mechanistic information available, and on Charton analyses using two preceding generations of iridium catalysts developed for this highly challenging transformation. Sterically unbiased chiral aldehydes that were not accessible previously have been obtained with high levels of enantioselectivity, thus validating the initial hypothesis regarding the selected ligand-design elements. A rationale for the high enantioselectivities achieved in most cases is also presented. Achieving enantioselectivity: An improved generation of chiral cationic iridium catalysts for the asymmetric isomerization of primary allylic alcohols is disclosed. The design of these air-stable complexes relies on preliminary mechanistic information and on Charton analyses using two preceding generations of iridium catalysts developed for this highly challenging transformation (see figure).

Processes for the Manufacture of Chiral and Racemic Forms of 3-Aminotetrahydrofurans, Their Salts and Derivatives

A novel process for the synthesis of (S)-3-Amino-tetrahydrofuran and (R)-3-Amino-tetrahydrofuran is described. The process is applicable for substituted chiral-3-aminotetrahydrofuran derivatives.