163210-82-0

Basic information

• Product Name: (S)-2-Amino-4-pentenoic acid t-butyl ester
• Synonyms: (S)-2-Amino-4-pentenoic acid t-butyl ester;(S)-2-allylglycine tert-butyl ester;tert-butyl (S)-2-aminopent-4-enoate;4-Pentenoic acid, 2-amino-, 1,1-dimethylethyl ester, (2S)-;S-Allylglycine 1,1-dimethylethyl ester
• CAS NO: 163210-82-0
• Molecular Formula: C₉H₁₇NO₂
• Molecular Weight: 171.24
• Product Categories: API intermediates
• Mol File: 163210-82-0.mol
• Article Data: 13

Chemical Properties

• Boiling Point: 193.5±0.0 °C at 760 mmHg
• Flash Point: 64.8±0.0 °C
• Appearance: /
• Density: 1.0±0.0 g/cm3
• Vapor Pressure: 0.5±0.0 mmHg at 25°C
• Refractive Index: 1.454
• CAS DataBase Reference: (S)-2-Amino-4-pentenoic acid t-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Amino-4-pentenoic acid t-butyl ester(163210-82-0)
• EPA Substance Registry System: (S)-2-Amino-4-pentenoic acid t-butyl ester(163210-82-0)

Safety Data

• Hazardous Substances Data: 163210-82-0(Hazardous Substances Data)

Usage

General Description

(S)-2-Amino-4-pentenoic acid t-butyl ester is a chemical compound consisting of a butyl ester of the amino acid (S)-2-amino-4-pentenoic acid. It is a derivative of the non-proteinogenic amino acid dehydroalanine, which is not found naturally in proteins but has important biological activities. The t-butyl ester group in this compound serves to protect the carboxylic acid functionality, making it more stable and enabling its use in various organic synthesis reactions. (S)-2-Amino-4-pentenoic acid t-butyl ester may have potential applications in pharmaceutical and medicinal chemistry, where the incorporation of non-proteinogenic amino acids and their derivatives can lead to the discovery of new drugs and therapeutic agents. Additionally, it may also have uses in the development of novel materials and as a tool in chemical biology research.

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

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

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 
• 1508298-39-2 (S)-tert-butyl 2-(4-methylphenylsulfonamido)-4-oxobutanoate 
• 1508298-40-5 (S)-tert-butyl 4,4-dimethoxy-2-(4-methylphenylsulfonamido)butanoate 
• 1508298-41-6 (S,E)-tert-butyl 2-(N-(4-bromobut-2-enyl)-4-methylphenylsulfonamido)-4,4-dimethoxybutanoate 
• 1508298-37-0 (S,E)-tert-butyl 2-(N-(4-bromobut-2-enyl)-4-methylphenylsulfonamido)-4-oxobutanoate 
• 1508298-36-9 (2S,3S,4S)-tert-butyl 3-formyl-1-tosyl-4-vinylpyrrolidine-2-carboxylate 
• 1508298-43-8 (2S,3R,4S)-tert-butyl 3-((E)-2-methoxyvinyl)-1-tosyl-4-vinylpyrrolidine-2-carboxylate 
• 1508298-44-9 (2S,3S,4S)-tert-butyl 3-(2-oxoethyl)-1-tosyl-4-vinylpyrrolidine-2-carboxylate 
• 1508298-49-4 (S,E)-tert-butyl 2-(N-(4-chloro-3-methylbut-2-enyl)-4-methylphenylsulfonamido)-4,4-dimethoxybutanoate 
• 1508298-42-7 (S,E)-tert-butyl 2-(N-(4-bromo-3-methylbut-2-enyl)-4-methylphenylsulfonamido)-4,4-dimethoxybutanoate 
• 1508298-50-7 (S,E)-tert-butyl 2-(N-(4-bromo-3-methylbut-2-enyl)-4-methylphenylsulfonamido)-4-oxobutanoate 
• 1508298-51-8 (2S,3S,4R)-tert-butyl 3-formyl-4-(prop-1-en-2-yl)-1-tosylpyrrolidine-2-carboxylate 
• 1508298-38-1 (S)-tert-butyl 2-(4-methylphenylsulfonamido)pent-4-enoate 

Relevant articles and documents

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.

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.

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.