(2S)-2-Azaniumyl-6-diazo-5-oxohexanoate

Base Information

• Chemical Name: (2S)-2-Azaniumyl-6-diazo-5-oxohexanoate
• CAS No.: 157-03-9
• Molecular Formula: C6H9 N3 O3
• Molecular Weight: 171.156
• Hs Code.: 2927000090
• Mol file: 157-03-9.mol

Synonyms:(2S)-2-Azaniumyl-6-diazo-5-oxohexanoate;CHEBI:183231;6-diazo-5-oxo-L-norleucine zwitterion

Chemical Property of (2S)-2-Azaniumyl-6-diazo-5-oxohexanoate

Chemical Property:

• Melting Point: -145oC (dec.)
• Refractive Index: 1.5800 (estimate)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 117.78000
• Density: g/cm³
• LogP: -0.17044
• Storage Temp.: −20°C
• Solubility.: DMSO (Slightly, Heated, Sonicated), Water (Slightly)
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 171.06439116
• Heavy Atom Count: 12
• Complexity: 227

Purity/Quality:

98%,99%, ^*data from raw suppliers

6-Diazo-5-oxo-L-norleucine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25
• Safety Statements: 36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C(CC(=O)C=[N+]=[N-])C(C(=O)[O-])[NH3+]
• Isomeric SMILES: C(CC(=O)C=[N+]=[N-])[C@@H](C(=O)[O-])[NH3+]
• Uses: 6-Diazo-5-oxo-L-norleucine (DON) has been used as an inhibitor of glutamine synthetase–glutamine(amide)-2-oxoglutarate aminotransferase.

Technology Process of (2S)-2-Azaniumyl-6-diazo-5-oxohexanoate

There total 20 articles about (2S)-2-Azaniumyl-6-diazo-5-oxohexanoate 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: 88.0%

6-Diazo-5-oxo-N-Tfa-L-norleucine-OMe (7589-24-4) → 6-diazo-5-oxo-L-norleucine (157-03-9,7390-76-3,764-17-0)

Guidance literature:

With sodium hydroxide; In methanol; for 0.5h; Ambient temperature;

DOI:10.1021/jo00153a026

Reference yield: 81.0%

ethyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-diazo-5-oxohexanoate (208520-02-9) → 6-diazo-5-oxo-L-norleucine (157-03-9,7390-76-3,764-17-0)

Guidance literature:

With piperidine; for 0.0333333h;

Reference yield: 52.0%

(S)-N-Fmoc-6-diazo-5-oxo-norleucine → 6-diazo-5-oxo-L-norleucine (157-03-9,7390-76-3,764-17-0)

Guidance literature:

With piperidine; for 0.0333333h; Inert atmosphere;

DOI:10.1016/j.tet.2010.04.080

upstream raw materials:

(S)-6-diazo-5-oxo-2-(2,2,2-trifluoro-acetylamino)-hexanoic acid ethyl ester

(2S)-2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanedioic acid α-methyl ester

6-Diazo-5-oxo-N-Tfa-L-norleucine-OMe

ethyl 2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-6-diazo-5-oxohexanoate

Downstream raw materials:

4-amino-4-deoxy-N¹⁰-methylpteroyl-(6-diazo-5-oxo)-L-norleucine