(-)-leukotoxin B

Base Information

• Chemical Name: (-)-leukotoxin B
• CAS No.: 32381-42-3
• Molecular Formula: C18H32O3
• UNII: FF156V3318
• DSSTox Substance ID: DTXSID001205124
• Metabolomics Workbench ID: 55828,201062
• Nikkaji Number: J532.640K
• Wikidata: Q7922031
• Wikipedia: Vernolic_acid
• Mol file: 32381-42-3.mol

Synonyms:12,13-epoxylinoleic acid;13-HPLA;13-hydroperoxylinoleic acid;cis-12-epoxyoctadeca-cis-9-enoate;cis-12-epoxyoctadeca-cis-9-enoic acid;vernoleate;vernolic acid

Chemical Property of (-)-leukotoxin B

Chemical Property:

• XLogP3: 5.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 14
• Exact Mass: 296.23514488
• Heavy Atom Count: 21
• Complexity: 299

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCC1C(O1)CC=CCCCCCCCC(=O)O
• Isomeric SMILES: CCCCC[C@H]1[C@H](O1)C/C=C\CCCCCCCC(=O)O

Technology Process of (-)-leukotoxin B

There total 14 articles about (-)-leukotoxin B 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:

(-)-leukotoxin B methyl ester (105229-02-5) → (-)-vernolic acid (32381-42-3,16833-57-1,7576-35-4)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1016/S0040-4039(00)84002-2

Reference yield:

(2S,3R)-3-Hydroxy-5-methoxy-tetrahydro-furan-2-carbaldehyde (105229-01-4,98050-07-8) → (-)-vernolic acid (32381-42-3,16833-57-1,7576-35-4)

Guidance literature:

Multi-step reaction with 8 steps

1: BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 deg C then 0 deg C, 12 h

2: H₂ / 5percent Pd/C / ethyl acetate / 1 h / 760 Torr

3: KH / tetrahydrofuran / 12 h

4: 1.) HOAc, H₂O 2.) LiN(SiCH₃)2 / 1.) THF, 60-65 deg C, 2 h 2.) THF/HMPA, -78 deg C, 12 h

6: pyridin / 34 h

7: Bu₄NF / tetrahydrofuran / 12 h

8: NaOH / methanol

With pyridine; sodium hydroxide; n-butyllithium; LiN(SiCH₃)2; tetrabutyl ammonium fluoride; water; hydrogen; potassium hydride; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; ethyl acetate;

DOI:10.1016/S0040-4039(00)84002-2

Reference yield:

(2R,3R)-5-Methoxy-2-((E)-pent-1-enyl)-tetrahydro-furan-3-ol (98050-08-9,98050-09-0,105198-52-5) → (-)-vernolic acid (32381-42-3,16833-57-1,7576-35-4)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / 5percent Pd/C / ethyl acetate / 1 h / 760 Torr

2: KH / tetrahydrofuran / 12 h

3: 1.) HOAc, H₂O 2.) LiN(SiCH₃)2 / 1.) THF, 60-65 deg C, 2 h 2.) THF/HMPA, -78 deg C, 12 h

5: pyridin / 34 h

6: Bu₄NF / tetrahydrofuran / 12 h

7: NaOH / methanol

With pyridine; sodium hydroxide; LiN(SiCH₃)2; tetrabutyl ammonium fluoride; water; hydrogen; potassium hydride; acetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; ethyl acetate;

DOI:10.1016/S0040-4039(00)84002-2

upstream raw materials:

(-)-leukotoxin B methyl ester

linoleic acid

methyl (9Z,12S,13R)-12,13-epoxy-9-octadecenoate

9-bromononanoic acid

Downstream raw materials:

(+/-)-cis-12,13-epoxy-9(Z)-octadecenoic acid