(2S,3R,4R)-2-amino-4-hydroxy-3-methylpentanoic acid

Base Information

• Chemical Name: (2S,3R,4R)-2-amino-4-hydroxy-3-methylpentanoic acid
• CAS No.: 21704-86-9
• Molecular Formula: C₆H₁₃NO₃
• Molecular Weight: 147.174
• European Community (EC) Number: 672-526-4
• Nikkaji Number: J35.791J
• Wikidata: Q105198775
• Mol file: 21704-86-9.mol

Synonyms:4-hydroxyisoleucine

Chemical Property of (2S,3R,4R)-2-amino-4-hydroxy-3-methylpentanoic acid

Chemical Property:

• Vapor Pressure: 1.11E-05mmHg at 25°C
• Melting Point: >200°C
• Refractive Index: 1.495
• Boiling Point: 332°C
• Flash Point: 147°C
• PSA: 83.55000
• Density: 1.181
• LogP: 0.11550
• XLogP3: -2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 147.08954328
• Heavy Atom Count: 10
• Complexity: 126

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(C)O)C(C(=O)O)N
• Isomeric SMILES: C[C@@H]([C@@H](C)O)[C@@H](C(=O)O)N
• Uses: Used as a treatment for type II diabetes

Technology Process of (2S,3R,4R)-2-amino-4-hydroxy-3-methylpentanoic acid

There total 68 articles about (2S,3R,4R)-2-amino-4-hydroxy-3-methylpentanoic acid 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: 98.0%

(3S,4R,5S)-3-amino-4,5-dimethyldihydrofuran-2(3H)-one (55527-86-1,168610-73-9,681230-42-2,695148-12-0,697797-11-8) + (3S,4R,5R)-3-Amino-4,5-dimethyl-dihydro-furan-2-one (55527-85-0,168610-73-9,681230-42-2,695148-12-0,697797-11-8) → (2S,3R,4S)-4-hydroxyisoleucine (55399-93-4,21704-86-9)

Guidance literature:

(3S,4R,5S)-3-amino-4,5-dimethyldihydrofuran-2(3H)-one; (3S,4R,5R)-3-Amino-4,5-dimethyl-dihydro-furan-2-one; With lithium hydroxide; water; at 20 ℃; for 2h;

With acetic acid;

Reference yield: 84.2%

L-isoleucine (73-32-5,959215-79-3,18875-42-8) → (2S,3R,4S)-4-hydroxyisoleucine (55399-93-4,21704-86-9)

Guidance literature:

With oxygen; α-ketoglutarate; iron(II) sulfate; sodium hydroxide; In aq. phosphate buffer; at 30 ℃; for 72h; pH=7; Temperature; pH-value; Reagent/catalyst; stereoselective reaction; Catalytic behavior; Green chemistry; Enzymatic reaction;

DOI:10.1021/acs.jafc.0c06544

Reference yield: 78.0%

(3S,4R,5S)-3-amino-4,5-dimethyl-3,4-dihydro-2(5H)-furanone hydrochloride (21704-91-6) → (2S,3R,4S)-4-hydroxyisoleucine (55399-93-4,21704-86-9)

Guidance literature:

With lithium hydroxide; In water; at 20 ℃; for 24h;

DOI:10.1002/1099-0690(200203)2002:5<834::AID-EJOC834>3.0.CO;2-6

upstream raw materials:

(3S,4R,5S)-3-amino-4,5-dimethyl-3,4-dihydro-2(5H)-furanone hydrochloride

2-Oxobutyric acid

acetaldehyde

(3SR,4RS,5SR)-3-amino-4,5-dimethyldihydrofuran-2-one

Downstream raw materials:

(3S,4S,5R)-3-amino-4,5-dimethyldihydrofuran-2(3H)-one

(3S,4R,5S)-3-amino-4,5-dimethyldihydrofuran-2(3H)-one

Refernces

• 1、 Du, Ping,Pan, Jiang,Qian, Xiao-Long,Xu, Jian-He,Yan, Shuai,Yu, Hui-Lei,Zhang, Zhi-Jun. "Engineering Bacillus subtilis Isoleucine Dioxygenase for Efficient Synthesis of (2 S,3 R,4 S)-4-Hydroxyisoleucine". . p. 14555 - 14563. Retrieved 2020.
• 2、 Sergent, Didier,Wang, Qian,Sasaki, N. Andre,Ouazzani, Jamal. "Synthesis of hydantoin analogues of (2S,3R,4S)-4-hydroxyisoleucine with insulinotropic properties". . p. 4332 - 4335. Retrieved 2008.
• 3、 Davidson, Madison,McNamee, Meredith,Fan, Ruixi,Guo, Yisong,Chang, Wei-Chen. "Repurposing Nonheme Iron Hydroxylases to Enable Catalytic Nitrile Installation through an Azido Group Assistance". supporting information. p. 3419 - 3423. Retrieved 2019/03/07.