Gomisin J

Base Information

• Chemical Name: Gomisin J
• CAS No.: 66280-25-9
• Molecular Formula: C22H28O6
• Molecular Weight: 388.461
• UNII: X13A57600T
• DSSTox Substance ID: DTXSID30216490
• Nikkaji Number: J476.691A
• Metabolomics Workbench ID: 129544
• ChEMBL ID: CHEMBL251864
• Mol file: 66280-25-9.mol

Synonyms:gomisin J

Chemical Property of Gomisin J

Chemical Property:

• Vapor Pressure: 2.12E-14mmHg at 25°C
• Melting Point: 148-149℃
• Boiling Point: 587.5°Cat760mmHg
• PKA: 8.97±0.60(Predicted)
• Flash Point: 309.1°C
• PSA: 77.38000
• Density: 1.161g/cm³
• LogP: 4.17000
• Storage Temp.: 2-8°C
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 388.18858861
• Heavy Atom Count: 28
• Complexity: 457

Purity/Quality:

95%-98% ^*data from raw suppliers

Gomisin J ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2=CC(=C(C(=C2C3=C(C(=C(C=C3CC1C)O)OC)OC)OC)OC)O
• Isomeric SMILES: C[C@@H]1CC2=CC(=C(C(=C2C3=C(C(=C(C=C3C[C@@H]1C)O)OC)OC)OC)OC)O
• Uses: Gomisin J is a promising drug for anti-ovarian cancer utilization. Also, it exhibits strong inhibition towards the glucuronidation of SN-8.

Technology Process of Gomisin J

There total 9 articles about Gomisin J 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: 100.0%

(6S,7R,S-Biar)-3,10-dibenzyloxy-5,6,7,8-tetrahydro-6,7-dimethyl-1,2,11,12-tetramethoxydibenzocyclooctene → (-)-gomisin J (66280-25-9)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 2h; Ambient temperature;

DOI:10.1016/0040-4020(95)00701-9

Reference yield: 95.0%

(6S,7R,S-Biar)-5,6,7,8-tetrahydro-3,10-dihydroxy-6,7-dimethyl-1,2,11,12-tetramethoxydibenzocyclooctene-4,9-dicarbaldehyde → (-)-gomisin J (66280-25-9)

Guidance literature:

With propylene glycol; toluene-4-sulfonic acid; In toluene; for 1.5h; Heating;

DOI:10.1016/0040-4020(95)00701-9

Reference yield:

(-)-deoxyschizandrin (61281-38-7,63598-55-0,63640-13-1,69176-53-0,101757-58-8,114488-89-0,115587-63-8,115587-64-9) → (-)-gomisin J (66280-25-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / trifluoroacetic acid / 24 h / Heating

2: 100 percent / BCl₃ / CH₂Cl₂ / 18 h / 0 °C

3: 84 percent / K₂CO₃ / dimethylformamide / 5 h / 70 °C

4: 87 percent / Rh(PPh₃)3Cl / toluene / 48 h / Heating

5: 100 percent / hydrogen / 10percent Pd-C / ethyl acetate / 2 h / Ambient temperature

With Wilkinson's catalyst; hydrogen; boron trichloride; potassium carbonate; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; trifluoroacetic acid;

DOI:10.1016/0040-4020(95)00701-9

upstream raw materials:

(3aR,S-Biar)-3a,4-dihydro-6,7,8,9,10,11-hexamethoxydibenzo<4,5:6,7>cycloocta<1,2-c>furan-1(3H)-one

(-)-deoxyschizandrin

Downstream raw materials:

(-)-deoxyschizandrin

Refernces