337518-87-3

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-BENZYL-4-(TERT-BUTOXY)-4-OXOBUTANOIC ACID is used as a building block for the synthesis of pharmaceutical compounds. Its unique structure allows for the development of new drugs with potential therapeutic applications, leveraging its reactivity and functional groups in medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, (S)-2-BENZYL-4-(TERT-BUTOXY)-4-OXOBUTANOIC ACID serves as an intermediate in the production of agrochemicals. Its role in the synthesis of various agrochemicals is crucial for developing effective products for crop protection and enhancement of agricultural yields.
Used in Specialty Chemicals Production:
(S)-2-BENZYL-4-(TERT-BUTOXY)-4-OXOBUTANOIC ACID is utilized in the creation of specialty chemicals, where its specific properties are harnessed to produce high-value compounds for niche applications across various industries.
Used as a Reagent in Organic Synthesis:
(S)-2-BENZYL-4-(TERT-BUTOXY)-4-OXOBUTANOIC ACID also functions as a reagent in organic synthesis, facilitating a range of chemical reactions that are essential for the preparation of complex organic molecules.
Potential Applications in New Materials Development:
(S)-2-BENZYL-4-(TERT-BUTOXY)-4-OXOBUTANOIC ACID may hold promise for the development of innovative materials, given its potential to be integrated into novel chemical structures with unique properties for various applications.

Upstream product

• 645-45-4 hydrocinnamic acid chloride 
• 127392-81-8 1-((3aS,6R,7aR)-8,8-dimethyl-2,2-dioxidohexahydro-1H-3a,6-methanobenzo[c]isothiazol-1-yl)-3-phenylpropan-1-one 
• 787635-22-7 1,1-dimethylethyl (3S)-4-[(3aS,6R,7aS)-8,8-dimethyl-2,2-dioxidotetrahydro-3a,6-methano-2,1-benzisothiazol-1(4H)-yl]-4-oxo-3-(phenylmethyl)butanoate 

Downstream Products

• 1449127-77-8 C₃₅H₄₂N₂O₅ 
• 1449127-78-9 C₃₆H₄₄N₂O₅ 
• 3972-36-9 (2S)-benzylsuccinic acid 

Relevant academic research and scientific papers

N-Thiazolylamide-based free fatty-acid 2 receptor agonists: Discovery, lead optimization and demonstration of off-target effect in a diabetes model

Free fatty acid-2 (FFA2) receptor is a G-protein coupled receptor of interest in the development of therapeutics in metabolic and inflammatory disease areas. The discovery and optimization of an N-thiazolylamide carboxylic acid FFA2 agonist scaffold is described. Dual key objectives were to i) evaluate the potential of this scaffold for lead optimization in particular with respect to safety de-risking physicochemical properties, i.e. lipophilicity and aromatic content, and ii) to demonstrate the utility of selected lead analogues from this scaffold in a pertinent in vivo model such as oral glucose tolerance test (OGTT). As such, a concomitant improvement in bioactivity together with lipophilic ligand efficiency (LLE) and fraction sp3 content (Fsp3) parameters guided these efforts. Compound 10 was advanced into studies in mice on the basis of its optimized profile vs initial lead 1 (ΔLLE = 0.3, ΔFsp3 = 0.24). Although active in OGTT, 10 also displayed similar activity in the FFA2-knockout mice. Given this off-target OGTT effect, we discontinued development of this FFA2 agonist scaffold.

A practical and efficient preparation of (S)-2-benzylsuccinic acid: A key acid synthon of KAD-1229

This report describes a practical and an efficient synthesis of (S)-2-benzyl-succinic acid, which was employed as a key intermediate for hypoglycemic KAD-1229 by means of asymmetric alkylation of N-acylsultam. The condensation of D-(-)-camphorsultam with 3-phenylpropionyl chloride gave N-acylsultam 1. N-acylsultam 1 reacted with 1.1 equimolar amount of sodium amide base to form chiral enolate, followed by alkylation with tert-butyl bromoacetate to afford 2. Cleavage of ester and saponification with H 2O2-LiOH provided the desired compound 5 with excellent yield and high optical purity.