20626-49-7

Basic information

• Product Name: (R)-2-methylbut-3-enoic acid
• Synonyms: (R)-2-methylbut-3-enoic acid;(2R)-2-Methylbut-3-enoic acid;EOS-61721
• CAS NO: 20626-49-7
• Molecular Formula: C₅H₈O₂
• Molecular Weight: 100.11582
• Mol File: 20626-49-7.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (R)-2-methylbut-3-enoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-methylbut-3-enoic acid(20626-49-7)
• EPA Substance Registry System: (R)-2-methylbut-3-enoic acid(20626-49-7)

Safety Data

• Hazardous Substances Data: 20626-49-7(Hazardous Substances Data)

Upstream product

• 249553-80-8 (2S,3R)-(+)-2-Amino-3-methylpent-4-enoic acid 

Downstream Products

• 1422508-61-9 methyl N-[(10R,14S)-14-[4-(3-chloro-2,6-difluorophenyl)-2,3-dioxopiperazin-1-yl]-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.0^2,7]nonadeca-1⁽¹⁹⁾,2⁽⁷⁾,3,5,15,17-hexaen-5-yl]carbamate trifluoroacetate 
• 1422511-19-0 methyl N-[(10R,14S)-14-[({[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]carbamoyl}methyl)amino]-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.0^2,7]nonadeca-1⁽¹⁹⁾,2⁽⁷⁾,3,5,15,17-hexaen-5-yl]carbamate 
• 1422511-20-3 methyl N-[(10R,14S)-14-[2-chloro-N-({[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]carbamoyl}methyl)acetamido]-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.0^2,7]nonadeca-1⁽¹⁹⁾,2⁽⁷⁾,3,5,15,17-hexaen-5-yl]carbamate 
• 1422508-65-3 methyl N-[(10R)-14-{4-[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]-2,5-dioxopiperazin-1-yl}-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.0^2,7]nonadeca-1⁽¹⁹⁾,2⁽⁷⁾,3,5,15,17-hexaen-5-yl]carbamate trifluoroacetate 
• 1422508-63-1 methyl N-[(10R)-14-{4-[3-chloro-2-fluoro-6-(trifluoromethyl)phenyl]-2,5-dioxopiperazin-1-yl}-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.02,7]nonadeca-1⁽¹⁹⁾,2⁽⁷⁾,3,5,15,17-hexaen-5-yl]carbamate trifluoroacetate 
• 1422510-93-7 tert-butyl N-[(1S)-1-(4-{4-[(methoxycarbonyl)amino]-2-[(2R)-2-methylbut-3-enamido]phenyl}-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)but-3-en-1-yl]carbamate 
• 1422510-94-8 tert-butyl N-[(1S)-1-(4-{4-[(methoxycarbonyl)amino]-2-[(2S)-2-methylbut-3-enamido]phenyl}-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)but-3-en-1-yl]carbamate 
• 1422387-17-4 methyl N-(4-{2-[(1S)-1-{[(tert-butoxy)carbonyl]amino}but-3-en-1-yl]pyridin-4-yl}-3-((2R)-2-methylbut-3-enamido)phenyl)carbamate 
• 1422511-12-3 tert-butyl N-[1-(2-methoxy-5-{4-[(methoxycarbonyl)amino]-2-[(2R)-2-methylbut-3-enamido]phenyl}pyridin-3-yl)but-3-en-1-yl]carbamate 
• 1422387-69-6 2-oxopropyl N-[(10R,14S)-14-[1-(3-chloro-2-fluorophenyl)-5-methyl-1H-1,2,3-triazole-4-amido]-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.0^2,7]nonadeca-1⁽¹⁹⁾,2⁽⁷⁾,3,5,15,17-hexaen-5-yl]carbamate 
• 1422448-80-3 1-(3-chloro-2-fluorophenyl)-N-[(10R,14S)-5-{[(1Z)-(cyanoimino)(phenoxy)methyl]amino}-10-methyl-9-oxo-8,16-diazatricyclo[13.3.1.0^2,7]nonadeca-1⁽¹⁹⁾,2⁽⁷⁾,3,5,15,17-hexaen-14-yl]-5-methyl-1H-1,2,3-triazole-4-carboxamide 

Relevant articles and documents

Action of L-aminoacylase and L-amino acid oxidase on 2-amino-3- methylpent-4-enoic acid [Δ(4)-dehydroisoleucine and alloisoleucine] stereoisomers: An alternative route to a stereochemically pure compound and the application to the synthesis of (R)-2-methylbutan-1-ol

The action of L-aminoacylase and L-amino acid oxidase on the stereoisomers of 2-amino-3-methylpent-4-enoic acid was examined, to secure stereochemically pure compounds related to L-alloisoleucine. A scalemic mixture [(2S,3R)- (90.0%), (2S,3S)(3.2%), (2R,3S)- (5.9%), (2R,3R)- (0.9%)] of the N-trifluoroacetyl derivatives of the title compound, which was prepared by an asymmetric Claisen rearrangement, was submitted to Aspergillus L-aminoacylase-catalyzed hydrolysis. Only the (2S,3R)- and (2S,3S)isomers were hydrolyzed to give the corresponding amino acids. The subsequent treatment of these isomers with Crotalus adamanteus L-amino acid oxidase afforded the pure (2S,3R)-isomer, related to L-alloisoleucine, in more than 99% stereochemically pure form. Moreover, the product was converted to L- alloisoleucine and (R)-2-methylbutan-1-ol via a chemoenzymatic procedure.