151436-20-3

Basic information

• Product Name: 4-Pentenoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (S)-
• CAS NO: 151436-20-3
• Molecular Formula: C14H25NO4
• Mol File: 151436-20-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 4-Pentenoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Pentenoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (S)-(151436-20-3)
• EPA Substance Registry System: 4-Pentenoic acid, 2-[[(1,1-dimethylethoxy)carbonyl]amino]-, 1,1-dimethylethyl ester, (S)-(151436-20-3)

Safety Data

• Hazardous Substances Data: 151436-20-3(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 16338-48-0 L-allylglycine 
• 203127-16-6 O-benzyl tert-butyl glyoxylate oxime ether 
• 1286768-92-0 (S)-2-Boc-aziridine-2-carboxylic acid 
• 90048-49-0 tert-butyl (2S)-2-amino-3-hydroxypropanoate 
• 59859-77-7 2-benzyloxycarbonylamino-3-hydroxy-propionic acid tert-butyl ester 
• 126496-79-5 (S)-N-tert-butoxycarbonyl aziridine-2-carboxylate methyl ester 
• 90600-20-7 (2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid 
• 75-65-0 tert-butyl alcohol 
• 1779-49-3 Methyltriphenylphosphonium bromide 
• 81323-59-3 tert-butyl (2S)-2-[(tert-butoxycarbonyl)amino]-4-oxobutanoate 
• 1826-67-1 vinyl magnesium bromide 
• 178602-42-1 di-tert-butyl (S)-aziridine-1,2-dicarboxylate 
• 163210-82-0 (S)-2-allylglycine tert-butyl ester 

Downstream Products

• 90600-20-7 (2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid 
• 116613-81-1 (S)-tert-butyl (1-hydroxypent-4-en-2-yl)carbamate 

Relevant articles and documents

Synthesis of Unsaturated α-Amino Acids using the Ramberg-Baecklund Reaction

A novel, and potentially versatile, procedure for the preparation of unsaturated α-amino acids in homochiral form is illustrated by the conversion of methionine into allylglycine (as its Boc, tert-butyl ester derivative) using the Ramberg-Baecklund reaction in the key step.

Synthesis of isotopically labelled amino acids

An efficient approach to the enantioselective synthesis of a series of amino acids from either bromoacetyl bromide or glycine is described using a [2,3]-sigmatropic rearrangement to establish the stereogenic centre at C-2 under mild conditions. Protected allylglycine 5 is a valuable building block to several amino acids e.g. hydrolytic cleavage of the auxiliary in 5 followed by deprotection gave L-allylglycine in 92% yield whilst oxidative cleavage of the terminal alkene followed by deprotection gave L-aspartic acid in 67% yield over the 2 steps. Furthermore alkene 5 may be converted to hydroxy ester 8 which is an intermediate for the synthesis of various amino acids including L-lysine and L-proline. Since the enantiomer of sultam 1 is commercially available, the analogous D-amino acids may be synthesised. This chemistry is readily adapted for the incorporation of isotopic labels for example for the synthesis of [1,2-13C2,15N]-L-homoserine 14. Copyright

Stereoselective synthesis of allyl- and homoallylglycines

A new method for the synthesis of N-protected allyl- and homoallylglycines was developed from aspartic and glutamic acid derivatives. The carboxylic side-chains of aspartic and glutamic derivatives was first transformed into the Weinreb amide by coupling with N,O-dimethylhydroxylamine and then reduced into the corresponding aldehyde. The latter could react with methyl-triphenylphosphonium bromide to yield the title compounds with 50% total yield.