4-Pentenoic acid, 2-amino-4-methyl-

Base Information

• Chemical Name: 4-Pentenoic acid, 2-amino-4-methyl-
• CAS No.: 28024-78-4
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.15700
• Mol file: 28024-78-4.mol

Synonyms:2-Amino-4-methyl-pent-4-enoic acid;α-methallylglycine;2-Amino-4-methyl-4-pentenoic acid;4,5-Didehydro-DL-leucine;2-amino-4-methylpent-4-enoic acid;4,5-dehydro-DL-leucine;methallyl glycine;

Chemical Property of 4-Pentenoic acid, 2-amino-4-methyl-

Chemical Property:

• PSA: 63.32000
• LogP: 1.06480

Purity/Quality:

98.5% ^*data from raw suppliers

2-Amino-4-methyl-4-pentenoicacid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-Pentenoic acid, 2-amino-4-methyl-

There total 9 articles about 4-Pentenoic acid, 2-amino-4-methyl- which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(R,S)-2-acetamido-4-methyl-4-pentenoic acid (87325-65-3,88547-24-4) → DL-γ,δ-didehydroleucine (28024-78-4,905929-81-9)

Guidance literature:

(R,S)-2-acetamido-4-methyl-4-pentenoic acid; With sodium hydroxide; In water; for 4h; Reflux; Inert atmosphere;

With hydrogenchloride; In water; pH=7; Inert atmosphere;

With ammonium hydroxide; Dowex-50 (H⁺); In water; Inert atmosphere;

DOI:10.1021/jo900459f

Reference yield: 81.0%

2-amino-2-hydroxyacetic acid (4746-62-7) + 4,4,5,5-tetramethyl-2-(2-methylallyl)-1,3,2-dioxaborolane (167773-10-6) → DL-γ,δ-didehydroleucine (28024-78-4,905929-81-9)

Guidance literature:

With triethylamine; In methanol; at 20 ℃; for 18h;

DOI:10.1139/v05-096

Reference yield:

ethyl 2-acetamido-2-cyano-4-methyl-4-pentenoate (20850-33-3) → DL-γ,δ-didehydroleucine (28024-78-4,905929-81-9)

Guidance literature:

With sodium hydroxide; (+-)-2-amino-4-methyl-4-pentenoic acid;

upstream raw materials:

ethyl 2-acetamido-2-cyano-4-methyl-4-pentenoate

2-Oximino-4-methyl-4-pentensaeureethylester

2-Oximino-4-methyl-4-pentensaeure

(R,S)-2-acetamido-4-methyl-4-pentenoic acid

Downstream raw materials:

3-amino-5,5-dimethyltetrahydro-2-furanone (hydrochloride)

Fmoc-4,5-didehydro-DL-leucine

2-benzoylamino-4-methyl-pent-4-enoic acid

Refernces

• 1、 Sugiura, Masaharu,Mori, Chieko,Hirano, Keiichi,Kobayashi, Shu. "Direct synthesis of unprotected α-amino acids via allylation of hydroxyglycine". . p. 937 - 942. Retrieved 2007/10/03.
• 2、 Hasegawa, Hiroshi,Shinohara, Yoshihiko,Baba, Shigeo. "Synthesis of 2>Leu-enkephalin and 2,D-Leu5>Leu-enkephalin with High Specific Tritiated Activity in the Leucine Residue". . p. 2641 - 2644. Retrieved 2007/10/02.