Trichothec-9-ene-3,4,8,15-tetrol, 12,13-epoxy-, 3,4,15-triacetate, (3alpha,4beta,8alpha)-

Base Information

• Chemical Name: Trichothec-9-ene-3,4,8,15-tetrol, 12,13-epoxy-, 3,4,15-triacetate, (3alpha,4beta,8alpha)-
• CAS No.: 68165-53-7
• Molecular Formula: C21H28O9
• Molecular Weight: 424.44
• DSSTox Substance ID: DTXSID50987670
• Wikidata: Q82975984
• ChEMBL ID: CHEMBL357529
• Mol file: 68165-53-7.mol

Synonyms:68165-53-7;Trichothec-9-ene-3,4,8,15-tetrol, 12,13-epoxy-, 3,4,15-triacetate, (3alpha,4beta,8alpha)-;CHEMBL357529;DTXSID50987670;8-Hydroxy-12,13-epoxytrichothec-9-ene-3,4,15-triyl triacetate

Chemical Property of Trichothec-9-ene-3,4,8,15-tetrol, 12,13-epoxy-, 3,4,15-triacetate, (3alpha,4beta,8alpha)-

Chemical Property:

• Vapor Pressure: 6.73E-13mmHg at 25°C
• Boiling Point: 518.1°C at 760 mmHg
• Flash Point: 174.7°C
• PSA: 120.89000
• Density: 1.35g/cm³
• LogP: 0.66650
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 424.17333247
• Heavy Atom Count: 30
• Complexity: 821

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC2C(CC1O)(C3(C(C(C(C34CO4)O2)OC(=O)C)OC(=O)C)C)COC(=O)C
• Isomeric SMILES: CC1=C[C@@H]2[C@](C[C@@H]1O)([C@]3([C@@H]([C@H]([C@H]([C@@]34CO4)O2)OC(=O)C)OC(=O)C)C)COC(=O)C

Technology Process of Trichothec-9-ene-3,4,8,15-tetrol, 12,13-epoxy-, 3,4,15-triacetate, (3alpha,4beta,8alpha)-

There total 21 articles about Trichothec-9-ene-3,4,8,15-tetrol, 12,13-epoxy-, 3,4,15-triacetate, (3alpha,4beta,8alpha)- 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: 86.0%

Neosolaniol (36519-25-2) + acetic anhydride (108-24-7) → Diacetylneosolaniol (65725-06-6) + 8-acetyl-neosolaniol (65041-92-1) + 3α,4β,15-Triacetoxy-8α-hydroxy-12,13-epoxytrichothec-9-ene (68165-53-7)

Guidance literature:

With pyridine; Ambient temperature;

DOI:10.1021/jm00123a008

Reference yield:

C21H26O9 (1930-11-6) → C21H28O9 (68165-53-7)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -78 - 20 ℃; for 1h;

DOI:10.1039/C39900001200

Reference yield:

C17H26O5 (130819-41-9) → C21H28O9 (68165-53-7)

Guidance literature:

Multi-step reaction with 19 steps

1: Et₃N / toluene / 24 h / 110 °C

2: 2,6-lutidine / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 88 percent / NaIO₄ / OsO₄ / diethyl ether; H₂O / 18 h / Ambient temperature

4: H₅IO₆ / diethyl ether / 0.08 h / Ambient temperature

5: NaOMe / methanol / 0.5 h / Heating

6: pyridinium toluene-p-sulphonate (PPTS) / 12 h / Ambient temperature

7: tetrahydrofuran; hexane / 18 h / Heating

8: ethane-1,2-diol, pyridinium toluene-p-sulphonate (PPTS) / CH₂Cl₂ / 18 h / Heating

9: 81 percent / chromium trioxide, 3,5-dimethylpyrazole / CH₂Cl₂ / 1 h / Ambient temperature

10: 1.) KN(SiMe₃)2, 2.) 2-p-tolylsulphonyl-3-(p-nitrophenyl)oxaziridine / 1.) toluene, THF, 0 deg C, 1 h, 2.) from -78 deg C to RT

11: NaBH₄ / methanol / 0.5 h / 0 °C

12: 90 percent / pyridinium toluene-p-sulphonate (PPTS) / methanol / 48 h / Ambient temperature

13: 50 percent / m-chloroperbenzoic acid (MCPBA), Na₂HPO₄ / CH₂Cl₂ / 48 h / Ambient temperature

14: pyridine / diethyl ether

15: Bu₄NF*3H₂O / tetrahydrofuran / 48 h / Ambient temperature

16: pyridine

17: 85 percent / pyridinium toluene-p-sulphonate (PPTS) / ethyl acetate / 48 h / Ambient temperature

18: 72 percent / O₃ / CH₂Cl₂ / -78 - 20 °C

19: LiBu^s3BH / tetrahydrofuran / 1 h / -78 - 20 °C

With pyridine; 2,6-dimethylpyridine; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; sodium tetrahydroborate; sodium periodate; disodium hydrogenphosphate; tetrabutyl ammonium fluoride; sodium methylate; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; L-Selectride; ozone; ethylene glycol; 3-(4-nitrophenyl)-2-p-tolylsulfonyloxaziridine; periodic acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; osmium(VIII) oxide; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; toluene;

DOI:10.1039/C39900001200

upstream raw materials:

C₂₁H₂₆O₉

C₁₇H₂₆O₅

C₁₈H₂₆O₆

C₂₃H₄₂O₇Si

Downstream raw materials:

T-2 tetraol tetraacetate

Refernces

• 1、 Anderson, D. W.,Black, R. M.,Lee, C. G.,Pottage, C.,Rickard, R. L.,et al.. "Structure-Activity Studies of Trichothecenes: Cytotoxicity of Analogues and Reaction Products Derived from T-2 Toxine and Neosolaniol". . p. 555 - 562. Retrieved 2007/10/02.