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

Base Information

• Chemical Name: Trichothec-9-ene-4,15-diol, 12,13-epoxy-, 15-(5-((1,5-dioxo-5-(2-(trimethylsilyl)ethoxy)-2,4-hexadienyl)oxy)-3-methyl-2-pentenoate), (4beta,15(E(2E,4Z)))-
• CAS No.: 89016-44-4
• Molecular Formula: C₃₂H₄₆O₉Si
• Molecular Weight: 602.797
• Mol file: 89016-44-4.mol

Synonyms:88969-02-2;89015-95-2;89016-44-4;Trichothec-9-ene-4,15-diol, 12,13-epoxy-, 15-(5-((1,5-dioxo-5-(2-(trimethylsilyl)ethoxy)-2,4-hexadienyl)oxy)-3-methyl-2-pentenoate), (4beta,15(E(2E,4Z)))-;Trichothec-9-ene-4,15-diol, 12,13-epoxy-, 15-(5-((1,5-dioxo-5-(2-(trimethylsilyl)ethoxy)-2,4-hexadienyl)oxy)-3-methyl-2-pentenoate), (4beta,15(Z(2E,4Z)))-;Trichothec-9-ene-4,15-diol, 12,13-epoxy-, 15-(5-((1,6-dioxo-6-(2-trimethylsilyl)ethoxy)-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-((1,5-dioxo-5-(2-(trimethylsilyl)ethoxy)-2,4-hexadienyl)oxy)-3-methyl-2-pentenoate), (4beta,15(E(2E,4Z)))-

Chemical Property:

• Vapor Pressure: 1.39E-21mmHg at 25°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 15
• Exact Mass: 602.29110958
• Heavy Atom Count: 42
• Complexity: 1180

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC2C(CC1)(C3(C(CC(C34CO4)O2)O)C)COC(=O)C=C(C)CCOC(=O)C=CC=CC(=O)OCC[Si](C)(C)C
• Isomeric SMILES: CC1=CC2C(CC1)(C3(C(CC(C34CO4)O2)O)C)COC(=O)/C=C(\C)/CCOC(=O)/C=C/C=C/C(=O)OCC[Si](C)(C)C

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

There total 12 articles about Trichothec-9-ene-4,15-diol, 12,13-epoxy-, 15-(5-((1,5-dioxo-5-(2-(trimethylsilyl)ethoxy)-2,4-hexadienyl)oxy)-3-methyl-2-pentenoate), (4beta,15(E(2E,4Z)))- 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: 87.0%

1-<<2-(Trimethylsilyl)ethoxy>carbonyl>-4-carboxy-1,3-(Z,E)-butadiene (87729-23-5) + 12,13-Epoxytrichothec-9-ene-4β,15-diol 15-(5'-Hydroxy-3'-methyl-2'(E)-pentenoate), verrol (84412-91-9) → Verrucarin J Seco Acid 2-(Trimethylsilyl)ethyl Ester (89016-44-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 25 ℃; for 1h;

DOI:10.1021/jo00184a021

Reference yield:

2-(Trimethylsilyl)ethanol (2916-68-9) → Verrucarin J Seco Acid 2-(Trimethylsilyl)ethyl Ester (89016-44-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / DCC, DMAP / CH₂Cl₂ / 16 h / 25 °C

2: KO-t-Bu / 2-methyl-propan-2-ol; diethyl ether / 6 h / 25 °C

3: 87 percent / Diethyl azodicarboxylate, PPh₃ / tetrahydrofuran / 1 h / 25 °C

With dmap; potassium tert-butylate; dicyclohexyl-carbodiimide; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; dichloromethane; tert-butyl alcohol;

DOI:10.1021/jo00184a021

Reference yield:

(Dimethoxy-phosphoryl)-acetic acid 2-trimethylsilanyl-ethyl ester (89121-12-0) → Verrucarin J Seco Acid 2-(Trimethylsilyl)ethyl Ester (89016-44-4)

Guidance literature:

Multi-step reaction with 2 steps

1: KO-t-Bu / 2-methyl-propan-2-ol; diethyl ether / 6 h / 25 °C

2: 87 percent / Diethyl azodicarboxylate, PPh₃ / tetrahydrofuran / 1 h / 25 °C

With potassium tert-butylate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; tert-butyl alcohol;

DOI:10.1021/jo00184a021

upstream raw materials:

1-<<2-(Trimethylsilyl)ethoxy>carbonyl>-4-carboxy-1,3-(Z,E)-butadiene

12,13-Epoxytrichothec-9-ene-4β,15-diol 15-(5'-Hydroxy-3'-methyl-2'(E)-pentenoate), verrol

2-(Trimethylsilyl)ethanol

(Dimethoxy-phosphoryl)-acetic acid 2-trimethylsilanyl-ethyl ester

Downstream raw materials:

C₂₉H₃₈O₉

Verrucarin J Seco Acid