5-Hydroxy-4-oxonorvaline

Base Information

• Chemical Name: 5-Hydroxy-4-oxonorvaline
• CAS No.: 26911-39-7
• Molecular Formula: C5H9 N O4
• Molecular Weight: 147.131
• UNII: 786N6370WK
• DSSTox Substance ID: DTXSID20922417
• Nikkaji Number: J8.731I
• Wikidata: Q27266643
• Metabolomics Workbench ID: 104931
• ChEMBL ID: CHEMBL4206982
• Mol file: 26911-39-7.mol

Synonyms:2-amino-5-hydroxy-4-oxopentanoic acid;2-amino-5-hydroxylevulinic acid;5-hydroxy-2-aminolevulinic acid;5-hydroxy-4-oxo-L-norvaline;5-hydroxy-4-oxonorvaline;RI 331;RI-331

Chemical Property of 5-Hydroxy-4-oxonorvaline

Chemical Property:

• Vapor Pressure: 9.14E-07mmHg at 25°C
• Boiling Point: 363.8°C at 760 mmHg
• Flash Point: 173.8°C
• PSA: 100.62000
• Density: 1.409g/cm³
• LogP: -0.94990
• XLogP3: -4.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 147.05315777
• Heavy Atom Count: 10
• Complexity: 145

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C(C(C(=O)O)N)C(=O)CO
• Isomeric SMILES: C([C@@H](C(=O)O)N)C(=O)CO

Technology Process of 5-Hydroxy-4-oxonorvaline

There total 13 articles about 5-Hydroxy-4-oxonorvaline 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: 92.0%

4-<3-(formyloxy)-2-oxopropyl>-2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-one (152685-29-5) → (S)-2-amino-5-hydroxy-4-oxopentanoic acid (26911-39-7,117404-54-3)

Guidance literature:

In water; isopropyl alcohol; Ambient temperature;

DOI:10.1016/S0040-4039(00)73803-2

Reference yield:

(S)-2-Benzyloxycarbonylamino-5-hydroxy-4-oxo-pentanoic acid (157695-66-4) → (S)-2-amino-5-hydroxy-4-oxopentanoic acid (26911-39-7,117404-54-3)

Guidance literature:

With hydrogen; acetic acid; palladium on activated charcoal; In methanol; for 1h; under 2250.2 Torr; Yield given; Ambient temperature;

DOI:10.1055/s-1992-26142

Reference yield:

tert-butyl (S)-2-benzyloxycarbonylamino-4,5-dihydroxy-2-pentenoate (142683-57-6) → (S)-2-amino-5-hydroxy-4-oxopentanoic acid (26911-39-7,117404-54-3)

Guidance literature:

Multi-step reaction with 6 steps

2: 99 percent / H₂ / (R,R)-BF₄ / methanol / 12 h / 2250.2 Torr / Ambient temperature

3: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -55 deg C, 15 min, 2) to room temperature, 0.5 h

4: 95 percent / hydrogen fluoride-pyridine / acetonitrile / 4 h / Ambient temperature

5: TFA / 4 h / 0 °C

6: H₂, 10percent aq. HOAc / 5percent Pd/C / methanol / 1 h / 2250.2 Torr / Ambient temperature

With oxalyl dichloride; hydrogen; pyridine hydrogenfluoride; acetic acid; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; palladium on activated charcoal; (R,R)-⁺BF4^-; In methanol; acetonitrile;

DOI:10.1055/s-1992-26142

upstream raw materials:

L-N-Acetyl-δ-hydroxy-γ-oxonorvalin

(S)-2-Benzyloxycarbonylamino-5-hydroxy-4-oxo-pentanoic acid

4-<3-(formyloxy)-2-oxopropyl>-2,2-bis(trifluoromethyl)-1,3-oxazolidin-5-one

(S)-2,2-Bis(trifluormethyl)-4-(3-diazo-2-oxopropyl)-1,3-oxazolidin-5-on

Downstream raw materials:

3-hydroxy-2-[(2-hydroxy-4,4-dimethyl-6-oxocyclohex-1-en-1-yl)methyl]-5,5-dimethylcyclohex-2-en-1-one

L-Aspartic acid