Toxin IIc (Alternariaalternata)

Base Information

• Chemical Name: Toxin IIc (Alternariaalternata)
• CAS No.: 104420-17-9
• Molecular Formula: C₁₇H₂₄O₆
• Molecular Weight: 324.374
• Nikkaji Number: J427.510A,J427.512H,J826.160A
• Mol file: 104420-17-9.mol

Synonyms:Toxin IIc (Alternariaalternata);AF toxin IIc;104420-17-9;(2E,4E,6E,8R)-8-[(2R,3S)-2-hydroxy-3-methylpentanoyl]oxy-8-[(2S)-2-methyloxiran-2-yl]octa-2,4,6-trienoic acid;Toxin IIc;AF-toxin IIc;AF-Toxin II;AKOS040754230;(2E,8R)-8-[(S)-2-Methyloxiran-2-yl]-8-[[(2R,3S)-2-hydroxy-3-methylpentanoyl]oxy]-2,4,6-octatrienoic acid;2,4,6-Octatrienoic acid, 8-((2-hydroxy-3-methyl-1-oxopentyl)oxy)-8-(2-methyloxiranyl)-,(2S-(2R*(2E,4E,6E,8S*(2S*,3R*))))-

Chemical Property of Toxin IIc (Alternariaalternata)

Chemical Property:

• Vapor Pressure: 9.75E-13mmHg at 25°C
• Boiling Point: 514.5°C at 760 mmHg
• Flash Point: 183.3°C
• Density: 1.185g/cm³
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 324.15728848
• Heavy Atom Count: 23
• Complexity: 507

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)OC(C=CC=CC=CC(=O)O)C1(CO1)C)O
• Isomeric SMILES: CC[C@H](C)[C@H](C(=O)O[C@H](/C=C/C=C/C=C/C(=O)O)[C@@]1(CO1)C)O

Technology Process of Toxin IIc (Alternariaalternata)

There total 17 articles about Toxin IIc (Alternariaalternata) 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:

L-isoleucine (73-32-5,959215-79-3,18875-42-8) → AF-toxin IIc (104363-99-7,104420-16-8,104420-17-9,105089-13-2,108102-60-9)

Guidance literature:

Multi-step reaction with 8 steps

1: sodium nitrite

2: p-toluenesulphonic acid

3: lithium carbonate, water / methanol

4: imidazole / dimethylformamide

5: H₂ / palladium on carbon / ethanol

6: dicyclohexylcarbodiimide, 4-pyrrolidinopyridine / CH₂Cl₂

7: sodium hydride / aq. ethanol / Ambient temperature

8: tetrabutylammonium fluoride

With 1H-imidazole; tetrabutyl ammonium fluoride; water; hydrogen; lithium carbonate; sodium hydride; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; sodium nitrite; palladium on activated charcoal; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.34.2668

Reference yield:

(2S,3S)-2-(acetyloxy)-3-methylpentanoic acid (104973-58-2) → AF-toxin IIc (104363-99-7,104420-16-8,104420-17-9,105089-13-2,108102-60-9)

Guidance literature:

Multi-step reaction with 7 steps

1: p-toluenesulphonic acid

2: lithium carbonate, water / methanol

3: imidazole / dimethylformamide

4: H₂ / palladium on carbon / ethanol

5: dicyclohexylcarbodiimide, 4-pyrrolidinopyridine / CH₂Cl₂

6: sodium hydride / aq. ethanol / Ambient temperature

7: tetrabutylammonium fluoride

With 1H-imidazole; tetrabutyl ammonium fluoride; water; hydrogen; lithium carbonate; sodium hydride; 4-pyrrolidin-1-ylpyridine; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.34.2668

Reference yield:

benzyl (2S,3S)-2-acetoxy-3-methylpentanoate (104855-40-5) → AF-toxin IIc (104363-99-7,104420-16-8,104420-17-9,105089-13-2,108102-60-9)

Guidance literature:

Multi-step reaction with 6 steps

1: lithium carbonate, water / methanol

2: imidazole / dimethylformamide

3: H₂ / palladium on carbon / ethanol

4: dicyclohexylcarbodiimide, 4-pyrrolidinopyridine / CH₂Cl₂

5: sodium hydride / aq. ethanol / Ambient temperature

6: tetrabutylammonium fluoride

With 1H-imidazole; tetrabutyl ammonium fluoride; water; hydrogen; lithium carbonate; sodium hydride; 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1248/cpb.34.2668

upstream raw materials:

(2E,4E,6E)-(R)-8-[(2S,3S)-2-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-pentanoyloxy]-8-((S)-2-methyl-oxiranyl)-octa-2,4,6-trienoic acid

L-isoleucine

4-(tert-Butyldiphenylsiloxy)-5-methylhexa-2(E),5-dienal

4-(tert-Butyldiphenylsiloxy)-5-methylhexa-2(E),5-dien-1-ol

Refernces