4,15-Bis(acetyloxy)-3-hydroxy-12,13-epoxytrichothec-9-en-8-yl 3-hydroxy-3-methylbutanoate

Base Information

• Chemical Name: 4,15-Bis(acetyloxy)-3-hydroxy-12,13-epoxytrichothec-9-en-8-yl 3-hydroxy-3-methylbutanoate
• CAS No.: 84474-35-1
• Molecular Formula: C₂₄H₃₄O₁₀
• Molecular Weight: 482.528
• DSSTox Substance ID: DTXSID001004754
• Wikidata: Q105166550
• Mol file: 84474-35-1.mol

Synonyms:3'-Hydroxy T2 toxin;3'-Hydroxy-T-2 toxin;DTXSID001004754;Trichothec-9-ene-3,4,8,15-tetrol, 12,13-epoxy-, 4,15-diacetate 8-(3-hydroxy-3-methylbutanoate), (3-alpha,4-beta,8-alpha)-;LS-157015;4,15-Bis(acetyloxy)-3-hydroxy-12,13-epoxytrichothec-9-en-8-yl 3-hydroxy-3-methylbutanoate;[(2R,4S,7R,9R,10R,11S)-11-acetyloxy-2-(acetyloxymethyl)-10-hydroxy-1,5-dimethylspiro[8-oxatricyclo[7.2.1.02,7]dodec-5-ene-12,2'-oxirane]-4-yl] 3-hydroxy-3-methylbutanoate

Chemical Property of 4,15-Bis(acetyloxy)-3-hydroxy-12,13-epoxytrichothec-9-en-8-yl 3-hydroxy-3-methylbutanoate

Chemical Property:

• Vapor Pressure: 7.14E-17mmHg at 25°C
• Refractive Index: 1.561
• Boiling Point: 599.5°C at 760 mmHg
• Flash Point: 197.7°C
• PSA: 141.12000
• Density: 1.33g/cm³
• LogP: 0.80760
• XLogP3: -0.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 9
• Exact Mass: 482.21519728
• Heavy Atom Count: 34
• Complexity: 927

Purity/Quality:

99%min ^*data from raw suppliers

3'-HYDROXY-T-2 TOXIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2C(CC1OC(=O)CC(C)(C)O)(C3(C(C(C(C34CO4)O2)O)OC(=O)C)C)COC(=O)C
• Isomeric SMILES: CC1=C[C@@H]2[C@](C[C@@H]1OC(=O)CC(C)(C)O)(C3([C@@H]([C@H]([C@H](C34CO4)O2)O)OC(=O)C)C)COC(=O)C

Technology Process of 4,15-Bis(acetyloxy)-3-hydroxy-12,13-epoxytrichothec-9-en-8-yl 3-hydroxy-3-methylbutanoate

There total 7 articles about 4,15-Bis(acetyloxy)-3-hydroxy-12,13-epoxytrichothec-9-en-8-yl 3-hydroxy-3-methylbutanoate 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: 21.0%

C29H42O11 → 3'-Hydroxy T-2 toxin (84474-35-1,97373-18-7)

Guidance literature:

With pyridinium p-toluenesulfonate; In ethanol; for 1h; Heating;

DOI:10.1021/jo00391a063

Reference yield:

3-Hydroxy-3-methylbutyric acid (625-08-1) → 3'-Hydroxy T-2 toxin (84474-35-1,97373-18-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-dimethylaminopyridine, dicyclohexylcarbodiimide

2: ammonium hydroxide

With dmap; ammonium hydroxide; dicyclohexyl-carbodiimide;

DOI:10.1080/00021369.1982.10865484

Reference yield:

4β,15-diacetoxy-3α-(2-tetrahydropyranyloxy)scirpene → 3'-Hydroxy T-2 toxin (84474-35-1,97373-18-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 60 percent / SeO₂ / dioxane; H₂O / 22 h / Heating

2: Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 3 h / Ambient temperature

3: 21 percent / pyridinium tosylate / aq. ethanol / 1 h / Heating

With selenium(IV) oxide; pyridinium p-toluenesulfonate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; ethanol; water;

DOI:10.1021/jo00391a063

upstream raw materials:

3-Hydroxy-3-methylbutyric acid

4β,15-diacetoxy-3α-(2-tetrahydropyranyloxy)scirpene-8β-ol

Refernces

• 1、 Wani, Mansukh C.,Rector, Douglas H.,Cook, C. Edgar. "Synthesis of HT-2 Toxin, Neosolaniol, T-2 Toxin, 3'-Hydroxy T-2 Toxin, and Sporotrichiol from Anguidine by Routes Involving Hydroxyl Inversion/Esterification". . p. 3468 - 3470. Retrieved 2007/10/02.