Trichothec-9-ene-4,15-diol, 12,13-epoxy-, 15-(5-((6-ethoxy-1,6-dioxo-2,4-hexadienyl)oxy)-3-methyl-2-pentenoate), (4beta,15(2E,5(2E,4E)))-

Base Information

• Chemical Name: Trichothec-9-ene-4,15-diol, 12,13-epoxy-, 15-(5-((6-ethoxy-1,6-dioxo-2,4-hexadienyl)oxy)-3-methyl-2-pentenoate), (4beta,15(2E,5(2E,4E)))-
• CAS No.: 88969-00-0
• Molecular Formula: C₂₉H₃₈O₉
• Molecular Weight: 530.615
• Mol file: 88969-00-0.mol

Synonyms:88969-00-0;Trichothec-9-ene-4,15-diol, 12,13-epoxy-, 15-(5-((6-ethoxy-1,6-dioxo-2,4-hexadienyl)oxy)-3-methyl-2-pentenoate), (4beta,15(2E,5(2E,4E)))-

Chemical Property of Trichothec-9-ene-4,15-diol, 12,13-epoxy-, 15-(5-((6-ethoxy-1,6-dioxo-2,4-hexadienyl)oxy)-3-methyl-2-pentenoate), (4beta,15(2E,5(2E,4E)))-

Chemical Property:

• Vapor Pressure: 3.24E-20mmHg at 25°C
• XLogP3: 2.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 13
• Exact Mass: 530.25158279
• Heavy Atom Count: 38
• Complexity: 1070

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C=CC=CC(=O)OCCC(=CC(=O)OCC12CCC(=CC1OC3CC(C2(C34CO4)C)O)C)C
• Isomeric SMILES: CCOC(=O)/C=C/C=C/C(=O)OCC/C(=C/C(=O)OCC12CCC(=CC1OC3CC(C2(C34CO4)C)O)C)/C

Technology Process of Trichothec-9-ene-4,15-diol, 12,13-epoxy-, 15-(5-((6-ethoxy-1,6-dioxo-2,4-hexadienyl)oxy)-3-methyl-2-pentenoate), (4beta,15(2E,5(2E,4E)))-

There total 18 articles about Trichothec-9-ene-4,15-diol, 12,13-epoxy-, 15-(5-((6-ethoxy-1,6-dioxo-2,4-hexadienyl)oxy)-3-methyl-2-pentenoate), (4beta,15(2E,5(2E,4E)))- 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:

2,2,2-Trichloroethyl-5-(tert-butyltrimethylsilyloxy)-3-methyl-2(E)-pentenoate → C29H38O9 (88969-00-0)

Guidance literature:

Multi-step reaction with 7 steps

1: Zn, KH₂PO₄ / tetrahydrofuran / 16 h / 25 °C

2: 60 percent / DCC, DMAP / CH₂Cl₂ / 6 h / 25 °C

3: 97 percent / AcOH, H₂O / tetrahydrofuran / 5 h / 25 °C

4: 53 percent / DCC, DMAP / CH₂Cl₂ / 5 h / 25 °C

5: 57 percent / KO-t-Bu / 2-methyl-propan-2-ol / 3 h / 25 °C

6: 1) Pivaloyl chloride, Et₃N, 2) 4-Pyrrolidinopyridine / 1) CH₂Cl₂, 25 deg C, 2) 2.5h, 25 deg C

With dmap; potassium dihydrogenphosphate; potassium tert-butylate; water; pivaloyl chloride; 4-pyrrolidin-1-ylpyridine; acetic acid; triethylamine; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; dichloromethane; tert-butyl alcohol;

DOI:10.1021/jo00184a021

Reference yield:

(E)-4-tert-butyldimethylsilyloxy-1-iodo-2-methyl-1-butene (78592-77-5) → C29H38O9 (88969-00-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 75 percent / n-Butyllithium / diethyl ether / 1) Et₂O, -60 deg C 2) -78 deg C

2: 60 percent / DCC, DMAP / CH₂Cl₂ / 6 h / 25 °C

3: 97 percent / AcOH, H₂O / tetrahydrofuran / 5 h / 25 °C

4: 53 percent / DCC, DMAP / CH₂Cl₂ / 5 h / 25 °C

5: 57 percent / KO-t-Bu / 2-methyl-propan-2-ol / 3 h / 25 °C

6: 1) Pivaloyl chloride, Et₃N, 2) 4-Pyrrolidinopyridine / 1) CH₂Cl₂, 25 deg C, 2) 2.5h, 25 deg C

With dmap; n-butyllithium; potassium tert-butylate; water; pivaloyl chloride; 4-pyrrolidin-1-ylpyridine; acetic acid; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl alcohol;

DOI:10.1021/jo00184a021

Reference yield:

2,2,2-Trichloroethyl 5-Hydroxy-3-methyl-2(E)-pentenoate (88968-95-0) → C29H38O9 (88969-00-0)

Guidance literature:

Multi-step reaction with 8 steps

1: Imidazole / dimethylformamide / 22 h / 25 °C

2: Zn, KH₂PO₄ / tetrahydrofuran / 16 h / 25 °C

3: 60 percent / DCC, DMAP / CH₂Cl₂ / 6 h / 25 °C

4: 97 percent / AcOH, H₂O / tetrahydrofuran / 5 h / 25 °C

5: 53 percent / DCC, DMAP / CH₂Cl₂ / 5 h / 25 °C

6: 57 percent / KO-t-Bu / 2-methyl-propan-2-ol / 3 h / 25 °C

7: 1) Pivaloyl chloride, Et₃N, 2) 4-Pyrrolidinopyridine / 1) CH₂Cl₂, 25 deg C, 2) 2.5h, 25 deg C

With 1H-imidazole; dmap; potassium dihydrogenphosphate; potassium tert-butylate; water; pivaloyl chloride; 4-pyrrolidin-1-ylpyridine; acetic acid; triethylamine; dicyclohexyl-carbodiimide; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/jo00184a021

upstream raw materials:

ethanol

(E,E,E)-Verrucarin

p-Methoxybenzyl 2-(Trimethylsilyl)ethyl (E,Z)-Muconate

(E)-4-tert-butyldimethylsilyloxy-1-iodo-2-methyl-1-butene