149117-85-1

Basic information

• Product Name: ethyl (R)-2-[(tert-butoxycarbonyl)amino]pent-4-enoate
• Synonyms: ethyl (R)-2-[(tert-butoxycarbonyl)amino]pent-4-enoate
• CAS NO: 149117-85-1
• Molecular Weight: 243.303
• Mol File: 149117-85-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: ethyl (R)-2-[(tert-butoxycarbonyl)amino]pent-4-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl (R)-2-[(tert-butoxycarbonyl)amino]pent-4-enoate(149117-85-1)
• EPA Substance Registry System: ethyl (R)-2-[(tert-butoxycarbonyl)amino]pent-4-enoate(149117-85-1)

Safety Data

• Hazardous Substances Data: 149117-85-1(Hazardous Substances Data)

Upstream product

• 54594-06-8 D-allylglycine 
• 135722-56-4 ethyl (RS)-N-(tert-butoxycarbonyl)-2-aminopent-4-enoate 

Downstream Products

• 30724-02-8 hydroxyproline 
• 848488-70-0 tert-butyl (1R,4R)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate 
• 147266-92-0 (2R,4S )-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid 
• 659726-44-0 t-butyl (R)-N-(9-phenyl-9H-fluoren-9-yl)allylglycinate 
• 659726-45-1 ethyl (R)-N-(9-phenyl-9H-fluoren-9-yl)allylglycinate 

Relevant articles and documents

Epoxy amino acids produced from allylglycines intramolecularly cyclised to yield four stereoisomers of 4-hydroxyproline derivatives

Derivatives of 2-amino-4-pentenoic acid (allylglycine) were efficiently resolved using Subtilisin or acylase. The side-chain unsaturated bond of the enantiomerically pure amino acid with tert-butoxycarbonyl (Boc) protection was smoothly epoxidized with m-chloroperbenzoic acid. When the Boc protection of the amino group was removed, the amino group intramolecularly attacked the side-chain epoxide, generating compounds with five-membered rings: the 4-hydroxyproline derivatives. Two diastereomeric products were formed through the cyclisation reaction, for example, (2S,4S)-4-hydroxyproline benzyl ester (cis-8) and (2S,4R)-4-hydroxyproline benzyl ester (trans-8) were formed from (2S)-amino acid with a side-chain epoxide. Compound (2S,4S)-4-hydroxyproline benzyl ester (cis-8) was transformed to a lactone (cis-hydroxyproline lactone, 10) with the removal of benzyl alcohol. The cis-conformation was essential for the intramolecular ester exchange reaction; in fact, no lactone formation was observed for the trans isomer (trans-8). The separation of cis-hydroxyproline lactone and the trans-isomeric hydroxyproline benzyl ester was facile and clear, in contrast to the difficult separation of cis- and trans-hydroxyproline derivatives. Thus, two diastereomers of hydroxyproline derivatives for l-hydroxyproline and also for d-hydroxyproline were obtained, i.e., four diastereomers of hydroxyproline derivatives.

Iminoiodane mediated aziridination of α-allylglycine: Access to a novel rigid arginine derivative and to the natural amino acid enduracididine

The synthesis of fully protected aminodihydrohistidines in optically pure form is described starting from allylglycine derivatives. These compounds represent novel conformationally constrained analogues of arginine, one of them being, in addition, a protected form of the marine natural product, enduracididine. The key step of the strategy is a one-pot copper-catalyzed aziridination of t-butyl (S)-N-(9-phenyl-9H-fluoren-9-yl)allylglycinate ((S)-16) with 2-trimethylsilylethanesulfonamide in the presence of iodosylbenzene.