199588-89-1

Basic information

• Product Name: (R)-2-Amino-4-pentenoic acid t-butyl ester
• Synonyms: (R)-2-Amino-4-pentenoic acid t-butyl ester;R-Allylglycine 1,1-dimethylethyl ester
• CAS NO: 199588-89-1
• Molecular Formula: C9H17NO2
• Molecular Weight: 171.2368
• Product Categories: API intermediates
• Mol File: 199588-89-1.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 193.547 °C at 760 mmHg
• Flash Point: 64.843 °C
• Appearance: /
• Density: 0.953 g/cm3
• CAS DataBase Reference: (R)-2-Amino-4-pentenoic acid t-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-Amino-4-pentenoic acid t-butyl ester(199588-89-1)
• EPA Substance Registry System: (R)-2-Amino-4-pentenoic acid t-butyl ester(199588-89-1)

Safety Data

• Hazardous Substances Data: 199588-89-1(Hazardous Substances Data)

Usage

General Description

(R)-2-Amino-4-pentenoic acid t-butyl ester, also known as t-Butyl (R)-2-amino-4-pentenoate, is a chemical compound with the molecular formula C10H19NO2. It is a t-butyl ester derivative of the amino acid (R)-2-Amino-4-pentenoic acid. (R)-2-Amino-4-pentenoic acid t-butyl ester is commonly used in organic synthesis and as a building block in the production of pharmaceuticals, agrochemicals, and other fine chemicals. It is a clear, colorless liquid at room temperature and is known for its purity and stability, making it suitable for a wide range of applications in the chemical industry.

Upstream product

• 137896-97-0 tert-butyl 2-((diphenylmethylene)amino)pent-4-enoate 
• 81477-94-3 N-(diphenylmethylene)glycine tert-butyl ester 
• 27532-96-3 glycine tert-butyl ester hydrochloride 
• 6456-74-2 Glycine tert-butyl ester 
• 106-95-6 allyl bromide 
• 186749-71-3 N-benzyloxy-L-allylglycine tert-butyl ester 
• 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 
• 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 
• 1067975-40-9 glycine tert-butyl ester, p-chlorobenzaldehyde Schiff base 

Downstream Products

• 151436-20-3 tert-butyl (S)-2-[(tert-butoxycarbonyl)amino]pent-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 
• 1508298-47-2 (R)-MTPA 

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.