Sporidesmin

Base Information

• Chemical Name: Sporidesmin
• CAS No.: 1456-55-9
• Deprecated CAS: 1378-20-7,54868-51-8
• Molecular Formula: C₁₈H₂₀ClN₃O₆S₂
• Molecular Weight: 473.958
• UNII: H70LC3H0RW
• DSSTox Substance ID: DTXSID001030686,DTXSID60929900
• Nikkaji Number: J525.867G
• Wikidata: Q27108332
• Metabolomics Workbench ID: 164972
• Mol file: 1456-55-9.mol

Synonyms:isosporidesmin B;sporidesmin;sporidesmin A;sporidesmin B;sporidesmin C;sporidesmin D;sporidesmin E;sporidesmin F;sporidesmin G;sporidesmin H

Chemical Property of Sporidesmin

Chemical Property:

• Vapor Pressure: 2.28E-24mmHg at 25°C
• Melting Point: 179° (dependent on rate of heating)
• Boiling Point: 761.4°C at 760 mmHg
• PKA: 11.37±0.60(Predicted)
• Flash Point: 414.3°C
• PSA: 153.38000
• Density: 1.74g/cm³
• LogP: 0.74410
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 2
• Exact Mass: 473.0482054
• Heavy Atom Count: 30
• Complexity: 825

Purity/Quality:

98%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12C(=O)N3C4C(C(C3(C(=O)N1C)SS2)O)(C5=CC(=C(C(=C5N4C)OC)OC)Cl)O
• Isomeric SMILES: C[C@@]12C(=O)N3[C@@H]4[C@]([C@H]([C@]3(C(=O)N1C)SS2)O)(C5=CC(=C(C(=C5N4C)OC)OC)Cl)O
• Uses: Sporidesmin A is a toxin produced by the fungus Pithomyces chartarum which causes liver injury with inflammation and blockage of bile ducts in mammals.

Technology Process of Sporidesmin

There total 1 articles about Sporidesmin 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:

(4R)-11b,12c-diacetoxy-10-chloro-8,9-dimethoxy-2ξ-(4-methoxy-phenyl)-4,7,14-trimethyl-(6at,11bt)-6a,7,11b,12-tetrahydro-4,12a-azaethano-[1,3,5]dithiazepino[5',4':1,5]pyrrolo[2,3-b]indole-5,13-dione (50801-20-2) → sporidesmin A (1456-55-9,6781-30-2,50763-61-6)

Guidance literature:

Multistep reaction; (i) NaOH, aq. MeOH, (ii) MCPBA, CH₂Cl₂, (iii) BF₃-Et₂O;

DOI:10.1021/ja00800a079

Reference yield:

sporidesmin A (1456-55-9,6781-30-2,50763-61-6) → Sporidesmin E (22327-77-1)

Guidance literature:

With carbon disulfide; disulfane; In benzene;

DOI:10.1039/j39700000432

Reference yield:

acetic anhydride (108-24-7) + 4-methoxy-benzaldehyde (123-11-5) + sporidesmin A (1456-55-9,6781-30-2,50763-61-6) → (4R)-11b,12c-diacetoxy-10-chloro-8,9-dimethoxy-2ξ-(4-methoxy-phenyl)-4,7,14-trimethyl-(6at,11bt)-6a,7,11b,12-tetrahydro-4,12a-azaethano-[1,3,5]dithiazepino[5',4':1,5]pyrrolo[2,3-b]indole-5,13-dione (50801-20-2)

Guidance literature:

Multistep reaction; (i) NaBH₄, MeOH, (ii) /BRN= 471382/, BF₃-Et₂O, CH₂Cl₂, (iii) /BRN= 385737/, Py;

DOI:10.1021/ja00800a079

upstream raw materials:

(4R)-11b,12c-diacetoxy-10-chloro-8,9-dimethoxy-2ξ-(4-methoxy-phenyl)-4,7,14-trimethyl-(6at,11bt)-6a,7,11b,12-tetrahydro-4,12a-azaethano-[1,3,5]dithiazepino[5',4':1,5]pyrrolo[2,3-b]indole-5,13-dione

Downstream raw materials:

(4R)-11b,12c-diacetoxy-10-chloro-8,9-dimethoxy-2ξ-(4-methoxy-phenyl)-4,7,14-trimethyl-(6at,11bt)-6a,7,11b,12-tetrahydro-4,12a-azaethano-[1,3,5]dithiazepino[5',4':1,5]pyrrolo[2,3-b]indole-5,13-dione

Sporidesmin E

Refernces