163210-82-0

Usage

Uses

Used in Pharmaceutical and Medicinal Chemistry:
(S)-2-Amino-4-pentenoic acid t-butyl ester is used as a building block for the synthesis of novel compounds in pharmaceutical and medicinal chemistry. Its unique structure and the protective t-butyl ester group allow for the creation of new drugs and therapeutic agents that can address various medical conditions.
Used in the Development of Novel Materials:
(S)-2-Amino-4-pentenoic acid t-butyl ester is used as a precursor in the development of new materials. Its chemical properties and reactivity can be leveraged to produce materials with specific characteristics, such as improved stability or novel functionalities.
Used in Chemical Biology Research:
(S)-2-Amino-4-pentenoic acid t-butyl ester is used as a research tool in chemical biology. Its incorporation into biologically active molecules can provide insights into the mechanisms of action and potential applications of non-proteinogenic amino acids and their derivatives in biological systems.

InChI:InChI=1S/C9H17NO2/c1-5-6-7(10)8(11)12-9(2,3)4/h5,7H,1,6,10H2,2-4H3/t7-/m0/s1

Upstream product

• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 106-95-6 allyl bromide 
• 119244-19-8 tert-butyl (S)-2-[(diphenylmethylene)amino]pent-4-enoate 
• 98946-18-0 tert-Butyl 2,2,2-trichloroacetimidate 
• 146549-21-5 2-(9H-fluoren-9-ylmethoxycarbonylamino)-pent-4-enoic acid 
• 540-88-5 acetic acid tert-butyl ester 
• 137896-97-0 tert-butyl 2-((diphenylmethylene)amino)pent-4-enoate 
• 1025891-51-3 C₁₆H₂₀ClNO₂ 
• 203127-16-6 O-benzyl tert-butyl glyoxylate oxime ether 
• 186749-71-3 N-benzyloxy-L-allylglycine tert-butyl ester 

Downstream Products

• 151436-20-3 tert-butyl (S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoate 
• 1408282-66-5 tert-butyl (S)-N-(4-methoxyphenylsulfonyl)aminopent-4-enoate 
• 1408283-04-4 (S)-N₂-(4-methoxyphenylsulfonyl)-N₂-(3-pyridylmethyl)-2-aminopent-4-enehydroxamic acid 
• 1408282-96-1 O-tert-butyl (S)-N₂-(4-methoxyphenylsulfonyl)-N₂-(3-pyridylmethyl)-2-aminopent-4-enehydroxamate 
• 1408282-88-1 (S)-N-(4-methoxyphenylsulfonyl)-N-(3-pyridylmethyl)-2-aminopent-4-enoic acid 
• 1408282-80-3 tert-butyl (S)-N-(4-methoxyphenylsulfonyl)-N-(3-pyridylmethyl)-2-aminopent-4-enoate 
• 1508298-38-1 (S)-tert-butyl 2-(4-methylphenylsulfonamido)pent-4-enoate 
• 1508298-51-8 (2S,3S,4R)-tert-butyl 3-formyl-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate 
• 1508298-50-7 (S,E)-tert-butyl 2-(N-(4-bromo-3-methylbut-2-enyl)-4-methylphenylsulfonamido)-4-oxobutanoate 
• 1508298-42-7 (S,E)-tert-butyl 2-(N-(4-bromo-3-methylbut-2-enyl)-4-methylphenylsulfonamido)-4,4-dimethoxybutanoate 
• 1508298-49-4 (S,E)-tert-butyl 2-(N-(4-chloro-3-methylbut-2-enyl)-4-methylphenylsulfonamido)-4,4-dimethoxybutanoate 
• 1508298-44-9 (2S,3S,4S)-tert-butyl 3-(2-oxoethyl)-1-tosyl-4-vinylpyrrolidine-2-carboxylate 
• 1508298-43-8 (2S,3R,4S)-tert-butyl 3-((E)-2-methoxyvinyl)-1-tosyl-4-vinylpyrrolidine-2-carboxylate 
• 1508298-36-9 (2S,3S,4S)-tert-butyl 3-formyl-1-tosyl-4-vinylpyrrolidine-2-carboxylate 

Relevant academic research and scientific papers

Methylene Analogues of Neopetrosiamide as Potential Antimetastatic Agents: Solid-Supported Syntheses Using Diamino Diacids for Pre-Stapling of Peptides with Multiple Disulfides

Neopetrosiamide, a 28-residue peptide from Neopetrosia sp., contains three disulfide bonds and hinders mammalian tumor cell invasion. Proper connectivity of disulfide bonds is crucial for activity. Synthetic replacement of single disulfide bridges with methylene bridges gives active analogues. Pre-stapling of one ring enhances the correct formation of the remaining disulfides by reducing isomeric possibilities and possibly initiating the correct 3D fold. Cloning and expression of neopetrosiamide in E. coli affords access to the natural linear peptide.

A Unified Approach to Phytosiderophore Natural Products

This work reports on the concise total synthesis of eight natural products of the mugineic acid and avenic acid families (phytosiderophores). An innovative ?east-to-west“ assembly of the trimeric products resulted in a high degree of divergence enabling the formation of the final products in just 10 or 11 steps each with a minimum of overall synthetic effort. Chiral pool starting materials (l-malic acid, threonines) were employed for the outer building blocks while the middle building blocks were accessed by diastereo- and enantioselective methods. A highlight of this work consists in the straightforward preparation of epimeric hydroxyazetidine amino acids, useful building blocks on their own, enabling the first synthesis of 3’’-hydroxymugineic acid and 3’’-hydroxy-2’-deoxymugineic acid.

Pd/Cu dual catalysis: Highly enantioselective access to α-substituted α-amino acids and α-amino amides

The asymmetric allylation of glycine iminoesters has been accomplished through a synergistic Pd/Cu catalyst system, affording a range of α-substituted α-amino acids in high yields and with excellent enantioselectivities (88 → 99% ee). The introduction of a Cu-P,N-metallocenyl complex-activated glycine iminoester to the chiral palladium-catalyzed allylic allylation process is crucial owing to its high reactivity and excellent enantioselectivities. Importantly, this Pd/Cu dual catalysis strategy can be used for the asymmetric allylic alkylation of prochiral glycine amide derivatives, which could be further utilized to synthesize biologically important vicinal diamines.

Recoverable Dendritic Phase-Transfer Catalysts that Contain (+)-Cinchonine-Derived Ammonium Salts

Four new phosphorus dendrimeric phase-transfer catalysts are prepared that contain 12 (+)-cinchoninium salts on the surface obtained by the quaternisation of the quinuclidinic N atom. The asymmetric alkylation of a glycinate Schiff base with benzyl bromide is used as a benchmark reaction, and the dendrimeric catalyst that contains an allyl group on the O-9 hydroxy group of the cinchonine units is the most active. The recovery and reuse of the catalyst are possible for five consecutive runs without loss of activity and with only a slight decrease in enantioselectivity. If other electrophiles are used, substituted benzyl bromides give better results than other activated alkyl bromides to afford the corresponding R amino acid derivatives. A comparison of these results with those reported previously for similar cinchoninium salts shows that dendrimers could be a better support than other polymers for this type of organocatalysis.

Substrate stereocontrol in the intramolecular organocatalyzed tsuji-trost reaction: Enantioselective synthesis of allokainates

Organocatalyzed Tsuji-Trost cyclization of 3b proceeds with asymmetric induction and allows for stereoselective synthesis of (+)-allokainic acid. The stereochemical outcome of the cyclization was predicted by calculations.

Total synthesis and absolute configuration of the natural amino acid tetrahydrolathyrine

(Chemical Equation Presented) The natural product tetrahydrolathyrine has been synthesized through an iminoiodane-mediated aziridination of a (2S)-allylglycinol derivative, which provided a 2:3 mixture of diastereoisomers. One of these diastereoisomers wa

PROCESS FOR PRODUCTION OF MONO-SUBSTITUTED ALKYLATED COMPOUND USING ALDIMINE OR DERIVATIVE THEREOF

Disclosed is a process for producing an asymmetric mono-substituted alkylated compound of an α-amino acid which is represented by a specific formula by using an aldimine-type Schiff base. In the process, the alkylation of an aldimine-type Schiff base in a medium in the presence of an optically active quaternary ammonium salt phase transfer catalyst and an inorganic base is started, and subsequently the reaction is quenched at any time preceding the completion of the stoichimetrical reaction, thereby yielding a mono-substituted alkylated product having a high optical purity.

Evaluation of the Efficiency of the Chiral Quaternary Ammonium Salt β-Np-NAS-Br in the Organic-Aqueous Phase-Transfer Alkylation of a Protected Glycine Derivative

The inherent efficiency of the N-spiro C2-symmetric chiral quaternary ammonium salt (S,S)-3 [(S,S)-β-Np-NAS-Br] has been evaluated in the representative organic-aqueous liquid-liquid phase-transfer benzylation and allylation of glycine tert-but

Studies on the enantioselective synthesis of α-amino acids via asymmetric phase-transfer catalysis

In this paper, we describe investigations into the use of cinchona alkaloid-derived quaternary ammonium phase-transfer catalysts for the asymmetric alkylation of a benzophenone-derived glycine-imine. Utility of this process is demonstrated by the enantioselective synthesis of a range of α-amino acid esters.

A new class of asymmetric phase-transfer catalysts derived from Cinchona alkaloids - Application in the enantioselective synthesis of α-amino acids

A new class of Cinchona alkaloid-derived quaternary ammonium phase-transfer catalysts bearing a N-anthracenylmethyl function are presented. These catalysts show high stereocontrol in the asymmetric alkylation of a benzophenone-derived glycine-imine, and application of this process to the enantioselective synthesis of a range of α-amino acid esters (e.e. 67-94%) is investigated.