(2R,3S)-2-amino-3-methylpentanedioic acid

Base Information

• Chemical Name: (2R,3S)-2-amino-3-methylpentanedioic acid
• CAS No.: 63088-04-0
• Molecular Formula: C6H11NO4
• Molecular Weight: 161.15600
• Hs Code.: 2922499990
• European Community (EC) Number: 687-030-3
• Nikkaji Number: J854.235J
• Wikidata: Q27096288
• ChEMBL ID: CHEMBL1234042
• Mol file: 63088-04-0.mol

Synonyms:(2R,3S)-2-amino-3-methylpentanedioic acid;(2R,3S)-3-METHYLGLUTAMIC ACID;T3MG;6208-94-2;2s,3r-2-Amino-3-Methylpentanedioic Acid;(+/-)-threo-3-Methylglutamic acid;Tocris-0811;CHEMBL1234042;SCHEMBL12648478;63088-04-0;AKOS006328758;NCGC00024803-01;NCGC00024803-02;(2R,3S)-2-Amino-3-methylglutaric acid;SR-01000597445;SR-01000597445-1;Q27096288

Chemical Property of (2R,3S)-2-amino-3-methylpentanedioic acid

Chemical Property:

• Vapor Pressure: 3.51E-05mmHg at 25°C
• Boiling Point: 329.4oC at 760 mmHg
• PKA: 2.20±0.10(Predicted)
• Flash Point: 153oC
• PSA: 100.62000
• Density: 1.329g/cm3
• LogP: 0.20940
• Storage Temp.: Store at RT
• Solubility.: H2O: >1.5mg/dL
• XLogP3: -3.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 161.06880783
• Heavy Atom Count: 11
• Complexity: 168

Purity/Quality:

99% ^*data from raw suppliers

(+/-)-threo-3-MethylglutamicAcid ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(CC(=O)O)C(C(=O)O)N
• Isomeric SMILES: C[C@@H](CC(=O)O)[C@H](C(=O)O)N
• Uses: A highly selective and potent agonist for kainate receptors.

Technology Process of (2R,3S)-2-amino-3-methylpentanedioic acid

There total 5 articles about (2R,3S)-2-amino-3-methylpentanedioic 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: 65.0%

(2S,3R)-2-Dibenzylamino-3-methyl-pentanedioic acid (129397-27-9) → (+/-)-threo-3-methylglutamate (2445-97-8,6070-75-3,6208-94-2,33511-69-2,33511-70-5,63088-04-0,76318-75-7,97550-61-3,274255-87-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 50 ℃; for 0.5h;

DOI:10.1246/cl.1990.377

Reference yield: 64.0%

cis-3-methylpyroglutamic acid (76318-72-4) → threo-β-methylglutamic acid (63088-04-0,274255-87-7)

Guidance literature:

With hydrogenchloride; for 2.5h; Heating;

DOI:10.1021/jo00318a042

Reference yield:

(2R,3S)-2-Dibenzylamino-3-methyl-pentanedioic acid di-tert-butyl ester (129397-19-9) → (+/-)-threo-3-methylglutamate (2445-97-8,6070-75-3,6208-94-2,33511-69-2,33511-70-5,63088-04-0,76318-75-7,97550-61-3,274255-87-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / TFA / CH₂Cl₂ / 33 h / Ambient temperature

2: 65 percent / H₂ / Pd/C / ethanol / 0.5 h / 50 °C

With hydrogen; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane;

DOI:10.1246/cl.1990.377

upstream raw materials:

(2S,3R)-2-Dibenzylamino-3-methyl-pentanedioic acid

(2R,3S)-2-Dibenzylamino-3-methyl-pentanedioic acid di-tert-butyl ester

cis-3-methylpyroglutamic acid

2,2-diethyl 3-methyl-5-oxopyrrolidine-2,2-dicarboxylate

Downstream raw materials:

(2S,3R)-2-amino-3-methylpentanedioic acid

(2R,3S)-3-methylglutamic acid

N-(p-toluenesulfonyl)-threo-β-methylglutamic acid