Production Method 1

898823-65-9

96886-55-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Acetone ;  2 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ;  pH 3 - 4, rt → 0 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  3 h, 92 °C
1.4 Reagents: (±)-Propylene oxide Solvents: Ethanol ;  1 h, rt

Reference

Asymmetric Synthesis of α,α-Disubstituted α-Amino Acids by Diastereoselective Alkylation of Camphor-Based Tricyclic Iminolactone

Xu, Peng-Fei; Li, Shuo; Lu, Ta-Jung; Wu, Chen-Chang; Fan, Botao; et al, Journal of Organic Chemistry, 2006, 71(12), 4364-4373

Production Method 2

96886-55-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Methanol
1.2 -

Reference

Asymmetric synthesis of bis(α-methylamino acid) via a BPB-Ni(II)-Ala complex

Ye, Lingya; Wu, Hongli; Zhang, Xiaolong; Zhou, Jiadong; Cao, Fei; et al, Youji Huaxue, 2009, 29(8), 1282-1286

Production Method 3

96886-55-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Methanol

Reference

Asymmetric synthesis of γ-unsaturated amino acids using chiral auxiliary

Ye, Ling-Ya; Wu, Hong-Li; Zhang, Xiao-Long; Zhou, Jia-Dong; Cao, Fei; et al, Yingyong Huaxue, 2009, 26(3), 346-348

Production Method 4

191284-36-3

96886-55-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran ,  Water
1.2 Reagents: Lithium hydroxide Solvents: Tetrahydrofuran ,  Water

Reference

Asymmetric synthesis of α-methyl α-amino acids by diastereoselective alkylation of optically active 6-isopropyl-3-methyl-2,3-dihydro-6H-1,4-oxazin-2-ones

Chinchilla, Rafael; Falvello, Larry R.; Galindo, Nuria; Najera, Carmen, Angewandte Chemie, 1997, 36(9), 995-997

Production Method 5

1318776-55-4

96886-55-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Water ;  rt; rt → 0 °C
1.2 Reagents: Bromine ;  0 °C; 0 °C; 0 °C → 75 °C; 4 h, 75 °C
1.3 Reagents: Hydrochloric acid Solvents: Water ;  neutralized

Reference

Microbial whole cell-catalyzed desymmetrization of prochiral malonamides: practical synthesis of enantioenriched functionalized carbamoylacetates and their application in the preparation of unusual α-amino acids

Zhang, Li-Bin; Wang, De-Xian; Wang, Mei-Xiang, Tetrahedron, 2011, 67(31), 5604-5609

Production Method 6

96886-55-4

Reaction Conditions

Reference

Synthesis of Modified Partial Structures of the Bacterial Cell Wall. 2. Retarded Metabolism of Lipopeptides by Insertion of α-Substituted α-Amino Acids

Frauer, Alexandra; Mehlfuehrer, Michaela; Thirring, Klaus; Berner, Heinz, Journal of Organic Chemistry, 1994, 59(15), 4215-22

Production Method 7

96886-55-4

Reaction Conditions

Reference

(S)-2-[N-(N'-benzylprolyl)amino]benzophenone (BPB) - a reagent for the synthesis of optically pure α-amino acids

Belokon, I., Janssen Chimica Acta, 1992, 10(2), 4-12

Production Method 8

1443008-01-2

96886-55-4

90365-73-4

Reaction Conditions

1.1 Solvents: 1,4-Dioxane ,  Water ;  1 h, 100 °C

Reference

Synthesis of quaternary α-methyl α-amino acids by asymmetric alkylation of pseudoephenamine alaninamide pivaldimine

Hugelshofer, Cedric L.; Mellem, Kevin T.; Myers, Andrew G., Organic Letters, 2013, 15(12), 3134-3137

Production Method 9

96886-55-4

12093-10-6

Reaction Conditions

1.1 Reagents: Amberlyst 15 Solvents: Acetone ,  Water ;  16 h, pH 2 - 4, rt
1.2 Reagents: Ammonia Solvents: Water ;  rt

Reference

Stereoselective functionalisation of cis- and trans-2-ferrocenyl-3-pivaloyl-4-alkyl-1,3-oxazolidin-5-ones: asymmetric synthesis of (R)- and (S)-2-alkyl-2-aminopent-4-enoic acids and (2R,3S)-2-amino-2-methyl-3-hydroxy-3-phenylpropanoic acid

Alonso, Francisco; Davies, Stephen G.; Elend, Almut S.; Leech, Michael A.; Roberts, Paul M.; et al, Organic & Biomolecular Chemistry, 2009, 7(3), 527-536

Production Method 10

96886-55-4

96293-17-3

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Ethanol ,  Water

Reference

Asymmetric synthesis of α-methyl amino acids via alkylation of glycine, alanine and phenylalanine in chiral nickel(II) complexes

Belokon, Yu. N.; Chernoglazova, N. I.; Bakhmutov, V. I.; Garbalinskaya, N. S.; Belikov, V. M., Izvestiya Akademii Nauk SSSR, 1987, (12), 2798-804

Production Method 11

96886-55-4

96886-56-5

Reaction Conditions

1.1 Reagents: Hydrochloric acid ,  Water Solvents: Water

Reference

Preparation of optically pure α-methyl-α-amino acids via alkylation of the nickel(II) Schiff base of (R,S)-alanine with (S)-2-N-(N'-benzylprolyl)aminobenzaldehyde

Belokon, Y. N.; Chernoglazova, N. I.; Kochetkov, C. A.; Garbalinskaya, N. S.; Belikov, V. M., Journal of the Chemical Society, 1985, (1985), 171-2

Production Method 12

206184-21-6

96886-55-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Catalysts: (S,S)-TADDOL Solvents: Toluene
1.2 -

Reference

Asymmetric PTC C-alkylation catalyzed by chiral derivatives of tartaric acid and aminophenols. Synthesis of (R)- and (S)-α-methyl amino acids

Belokon, Yuri N.; Kochetkov, Konstantin A.; Churkina, Tatiana D.; Ikonnikov, Nikolai S.; Chesnokov, Alexey A.; et al, Journal of Organic Chemistry, 2000, 65(21), 7041-7048

Production Method 13

88820-87-5

96886-55-4

Reaction Conditions

1.1 Solvents: Water

Reference

A practical asymmetric synthesis of α-methyl α-amino acids using a chiral Cu-salen complex as a phase transfer catalyst

Belokon, Y. N.; Davies, R. G.; North, M., Tetrahedron Letters, 2000, 41(37), 7245-7248

Production Method 14

96886-55-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Methanol ,  Water ;  > 1 min, 20 - 60 °C

Reference

Rapid asymmetric synthesis of amino acids via NiII complexes based on new fluorine containing chiral auxiliaries

Saghyan, Ashot S.; Dadayan, Ani S.; Dadayan, Slavik A.; Mkrtchyan, Anna F.; Geolchanyan, Arpine V.; et al, Tetrahedron: Asymmetry, 2010, 21(24), 2956-2965

Production Method 15

96886-55-4

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Dimethylformamide ;  60 min, 45 - 50 °C
1.2 Reagents: Acetic acid Solvents: Water ;  neutralized
1.3 Reagents: Hydrochloric acid Solvents: Methanol ,  Water ;  50 °C

Reference

New chiral NiII complexes of Schiff's bases of glycine and alanine for efficient asymmetric synthesis of α-amino acids

Saghiyan, Ashot S.; Dadayan, Slavik A.; Petrosyan, Satenik G.; Manasyan, Luisa L.; Geolchanyan, Arpine V.; et al, Tetrahedron: Asymmetry, 2006, 17(3), 455-467

Production Method 16

213619-63-7

96886-55-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Acetic acid ,  Toluene
1.2 Solvents: Ethanol
1.3 Reagents: Ammonia Solvents: Water

Reference

Asymmetric synthesis of α-methyl α-amino acids through diastereoselective alkylation under mild reaction conditions of an iminic alanine template with a 1,2,3,6-tetrahydro-2-pyrazinone structure

Najera, Carmen; Abellan, Tomas; Sansano, Jose M., European Journal of Organic Chemistry, 2000, (15), 2809-2820

Production Method 17

191284-36-3

96886-55-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water ;  1 h, rt
1.2 Reagents: Lithium hydroxide Solvents: Tetrahydrofuran ,  Water ;  6 h, rt

Reference

New oxazinone and pyrazinone derivatives as chiral reagents for the asymmetric synthesis of α-amino acids

Abellan, Tomas; Chinchilla, Rafael; Galindo, Nuria; Najera, Carmen; Sansano, Jose M., Journal of Heterocyclic Chemistry, 2000, 37(3), 467-479

Production Method 18

96886-55-4

Reaction Conditions

Reference

Product subclass 7: 2-aminoalkanoic acids (α-amino acids)

Wolkenberg, S. E.; Garbaccio, R. M., Science of Synthesis, 2006, 20, 385-482

Production Method 19

96886-55-4

Reaction Conditions

1.1 Reagents: Hydrochloric acid Solvents: Water

Reference

General method for the asymmetric synthesis of α-amino acids via alkylation of the chiral nickel(II) Schiff base complexes of glycine and alanine

Belokon, Yu. N.; Bakhmutov, V. I.; Chernoglazova, N. I.; Kochetkov, K. A.; Vitt, S. V.; et al, Journal of the Chemical Society, 1988, (2), 305-12

Production Method 20

96886-55-4

Reaction Conditions

Reference

Synthesis of (optically active) sulfur-containing trifunctional amino acids by radical addition to (optically active) unsaturated amino acids

Broxterman, Quirinus B.; Kaptein, Bernard; Kamphuis, Johan; Schoemaker, Hans E., Journal of Organic Chemistry, 1992, 57(23), 6286-94

Production Method 21

1266681-06-4

96886-55-4

36482-69-6

Reaction Conditions

1.1 Reagents: Cesium hydroxide Solvents: Water ;  2 h, 70 °C
1.2 Reagents: Hydrochloric acid Solvents: Water ;  rt

Reference

Asymmetric synthesis of α-methyl-α-amino acids via diastereoselective alkylation of (1S)-(+)-3-carene derived tricyclic iminolactone

Lu, Ta-Jung; Lin, Cheng-Kun, Journal of Organic Chemistry, 2011, 76(6), 1621-1633

Production Method 22

144125-67-7

96886-55-4

144072-99-1

Reaction Conditions

1.1 Catalysts: Aminopeptidase Solvents: Water

Reference

Enzymic resolution of α,α-disubstituted α-amino acid esters and amides

Kaptein, Bernard; Boesten, Wilhelmus H. J.; Broxterman, Quirinus B.; Peters, Piet J. H.; Schoemaker, Hans E.; et al, Tetrahedron: Asymmetry, 1993, 4(6), 1113-16

(2S)-2-amino-2-methyl-pent-4-enoic acid Raw materials

• Alanine, N-(phenylmethylene)-, 1-methylethyl ester
• 1(2H)-Pyrazinecarboxylic acid, 3,6-dihydro-3-methyl-6-(1-methylethyl)-2-oxo-5-phenyl-3-(2-propen-1-yl)-, 1,1-dimethylethyl ester, (3S,6R)-
• R-(-)-benzyl 2-carbamyl-2-methylpent-4-enoate
• 2H-1,4-Oxazin-2-one, 3,6-dihydro-3-methyl-6-(1-methylethyl)-5-phenyl-3-(2-propen-1-yl)-, (3S,6R)-
• Cyclopropa[g]-1,4-benzoxazin-2(3H)-one, 5,5a,6,6a,7,7a-hexahydro-3,6,6,7a-tetramethyl-3-(2-propen-1-yl)-, (3S,5aR,6aS,7aS)-
• 4-Pentenamide, 2-amino-N-[(1S,2S)-2-hydroxy-1,2-diphenylethyl]-N,2-dimethyl-, (2S)-
• 4-Pentenoicacid,2-amino-2-methyl-,methylester,(2S)-(9CI)
• 4-Pentenamide, 2-amino-2-methyl-, (±)-
• (1S,2R,5S,8R)-5-allyl-5,8,11,11-tetramethyl-3-oxa-6-azatricyclo[6.2.1.02,7]undec-6-en-4-one

(2S)-2-amino-2-methyl-pent-4-enoic acid Preparation Products

• Ferrocenecarboxaldehyde (12093-10-6)
• (2R)-2-amino-2-methyl-pent-4-enoic acid (96886-56-5)
• Cα-methyl-D-allylglycinamide (144072-99-1)
• Bicyclo[4.1.0]heptan-3-one,4-hydroxy-4,7,7-trimethyl-, (1R,4S,6S)- (36482-69-6)
• (2S)-2-amino-2-methyl-pent-4-enoic acid (96886-55-4)
• (s)-n-(2-Benzoylphenyl)-1-benzylpyrrolidine-2-carboxamide (96293-17-3)
• (1S,2S)-2-(Methylamino)-1,2-diphenylethan-1-ol (90365-73-4)

• 1. Exchanged ligands on the surface of a giant cluster: [(MoO3)176(H2O)63(CH3OH)17Hn](32 – n)–
  Chem. Commun., 1998, 1501-1502
• 2. Dissociation of aryl sulfonyl phthalimide radical anions: relevance to the biological activity of arylsulfonyl amides?
  Abdelaziz Houmam,Emad M. Hamed Chem. Commun., 2012,48, 11328-11330
• 3. Excellent electrochemical performance of LiFe0.4Mn0.6PO4 microspheres produced using a double carbon coating process?
  Yong Ping Huang,Tao Tao,Zheng Chen,Wei Han,Ying Wu,Chunjiang Kuang,Shaoxiong Zhou,Ying Chen J. Mater. Chem. A, 2014,2, 18831-18837
• 4. Evolution of shape, size, and areal density of a single plane of Si nanocrystals embedded in SiO2 matrix studied by atom probe tomography
  Bin Han,Yasuo Shimizu,Gabriele Seguini,Celia Castro,Gérard Ben Assayag,Koji Inoue,Yasuyoshi Nagai,Sylvie Schamm-Chardon,Michele Perego RSC Adv., 2016,6, 3617-3622
• 5. Establishing plasmon contribution to chemical reactions: alkoxyamines as a thermal probe?
  Olga Guselnikova,Gérard Audran,Jean-Patrick Joly,Andrii Trelin,Evgeny V. Tretyakov,Vaclav Svorcik,Oleksiy Lyutakov,Sylvain R. A. Marque Chem. Sci., 2021,12, 4154-4161

• Solvents and Organic Chemicals Organic Compounds Organic acids and derivatives Carboxylic acids and derivatives Amino acids, peptides, and analogues Amino acids and derivatives
• Solvents and Organic Chemicals Organic Compounds Acids/Esters

Introduction to (2S)-2-amino-2-methyl-pent-4-enoic Acid (CAS No. 96886-55-4)

(2S)-2-amino-2-methyl-pent-4-enoic acid, with the CAS number 96886-55-4, is a significant compound in the field of chemical and pharmaceutical research. This enantiomerically pure compound has garnered attention due to its unique structural properties and potential applications in drug development and biochemical studies.

The molecular structure of (2S)-2-amino-2-methyl-pent-4-enoic acid consists of a five-carbon chain with an amine group at the second carbon and a methyl group at the same position, along with a double bond at the fourth carbon. This configuration imparts specific stereochemical characteristics, making it a valuable building block in organic synthesis and chiral chemistry.

In recent years, there has been growing interest in the applications of this compound, particularly in the development of novel pharmaceuticals. Its enantiomeric purity ensures that it can be used effectively in asymmetric synthesis, where the precise stereochemistry of molecules is crucial for their biological activity. For instance, many drugs on the market today are enantiomerically pure to enhance their efficacy and reduce side effects.

One of the most promising areas of research involving (2S)-2-amino-2-methyl-pent-4-enoic acid is its role as a precursor in the synthesis of bioactive molecules. Researchers have explored its utility in creating complex peptides and proteins, which are essential for various therapeutic applications. The compound's ability to serve as a chiral center allows for the construction of enantiomerically enriched libraries, which can be screened for potential drug candidates.

Recent studies have also highlighted the importance of this compound in understanding enzyme mechanisms and substrate specificity. By using (2S)-2-amino-2-methyl-pent-4-enoic acid as a substrate or inhibitor, scientists can gain insights into how enzymes interact with different molecular structures. This knowledge is crucial for designing more effective drugs that can target specific enzymatic pathways without affecting others.

The pharmaceutical industry has been particularly interested in exploring the therapeutic potential of derivatives of (2S)-2-amino-2-methyl-pent-4-enoic acid. For example, modifications to its side chains have led to the discovery of compounds with anti-inflammatory, analgesic, and even anticancer properties. These findings underscore the importance of this compound as a scaffold for drug discovery.

In addition to its pharmaceutical applications, (2S)-2-amino-2-methyl-pent-4-enoic acid has found utility in materials science and biotechnology. Its unique chemical properties make it suitable for use in polymer synthesis and as a chiral dopant in liquid crystals. These applications demonstrate the versatility of this compound beyond traditional medicinal chemistry.

The synthesis of (2S)-2-amino-2-methyl-pent-4-enoic acid has been optimized through various methods, including asymmetric hydrogenation and enzymatic resolution. These techniques ensure high yields and enantiomeric purity, which are critical for industrial-scale production. Advances in synthetic methodologies continue to enhance the accessibility of this valuable compound.

Future research directions may focus on expanding the applications of (2S)-2-amino-2-methyl-pent-4-enoic acid into new areas such as agrochemicals and environmental science. Its structural features could make it useful in developing novel pesticides or biodegradable materials. As our understanding of its properties grows, so too will its potential uses across multiple disciplines.

In conclusion, (CAS No. 96886-55) is a versatile and highly significant compound with broad applications in pharmaceuticals, materials science, and biotechnology. Its unique stereochemistry and reactivity make it an indispensable tool for researchers seeking to develop innovative solutions to complex problems.

• 96886-56-5((2R)-2-amino-2-methyl-pent-4-enoic acid)
• 749926-95-2(4-Pentenoic acid,2-amino-2,3-dimethyl-, (2S,3R)-)
• 6322-52-7(2-amino-2-methyldodec-11-enoic acid)
• 872983-37-4(4-Pentenoic acid, 2-amino-2-(2-hydroxyethyl)-)
• 191615-50-6(4-Pentenoic acid,2-amino-2,3-dimethyl-)
• 62377-89-3(4-Octenedioic acid, 2,7-diamino-2,7-diethyl-)
• 64298-91-5(4-Pentenoic acid,2-amino-2-methyl-)
• 16820-25-0((S)-2-AMINO-2-METHYL-4-PENTENOIC ACID)
• 587829-11-6(2-amino-2-(prop-2-en-1-yl)pent-4-enoic acid)
• 202351-49-3(4-Hexenoicacid,2-amino-2-methyl-,[R-(E)]-(9CI))