Ascofuranone

Base Information

• Chemical Name: Ascofuranone
• CAS No.: 38462-04-3
• Molecular Formula: C23H29ClO5
• Molecular Weight: 420.933
• UNII: I31EFB9515
• DSSTox Substance ID: DTXSID60903967
• Nikkaji Number: J20.605I
• Wikipedia: Ascofuranone
• Wikidata: Q4803989
• Metabolomics Workbench ID: 144682
• ChEMBL ID: CHEMBL133046
• Mol file: 38462-04-3.mol

Synonyms:ascofuranone

Chemical Property of Ascofuranone

Chemical Property:

• Vapor Pressure: 4.18E-14mmHg at 25°C
• Boiling Point: 581.2°C at 760 mmHg
• Flash Point: 305.3°C
• PSA: 83.83000
• Density: 1.207g/cm³
• LogP: 5.22400
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 420.1703517
• Heavy Atom Count: 29
• Complexity: 668

Purity/Quality:

99% ^*data from raw suppliers

(-)-Ascofuranone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(=C(C(=C1Cl)O)CC=C(C)CCC=C(C)C2CC(=O)C(O2)(C)C)O)C=O
• Isomeric SMILES: CC1=C(C(=C(C(=C1Cl)O)C/C=C(\C)/CC/C=C(\C)/[C@@H]2CC(=O)C(O2)(C)C)O)C=O
• Uses: (-)-Ascofuranone is an antibiotic with antitumor activity. It suppresses PMA-mediated matrix metalloproteinase-9 gene activation through the Ras/Raf/MEK/ERK- and Ap1-dependent mechanisms. (-)-Ascofuranone was effective in the treatment against Trypanosoma brucei brucei infection in mice.

Technology Process of Ascofuranone

There total 11 articles about Ascofuranone 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: 22.2%

(1''S,4''S)-(-)-ascofuranol (51759-79-6,99529-62-1) → Ascofuranone (38462-04-3)

Guidance literature:

With pyridinium chlorochromate; In dichloromethane; for 3h; Ambient temperature;

DOI:10.1016/S0040-4020(01)96657-8

Reference yield:

(2E,6E,1'S,4'S)-(+)-7-(4'-hydroxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl acetate (99529-56-3) → Ascofuranone (38462-04-3)

Guidance literature:

Multi-step reaction with 9 steps

1: imidazole / dimethylformamide / 6 h / Ambient temperature

2: 92.9 percent / K₂CO₃ / methanol; H₂O / 48 h / Ambient temperature

3: 1.26 g / n-BuLi, Ph₃CH, p-TsCl, LiCl / diethyl ether; hexamethylphosphoric acid triamide; hexane / 0.42 h / 0 °C

4: n-BuLi, HMPA / tetrahydrofuran; hexane / 0.75 h / -70 °C

5: 50.2 percent / CaCO₃, NCS / H₂O; dimethylformamide / Ambient temperature

6: 57 percent / DBU / tetrahydrofuran / 6 h / Heating

7: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min.

8: 71 percent / HF / acetonitrile; H₂O / 1 h / Ambient temperature

9: 22.2 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; N-chloro-succinimide; n-butyllithium; triphenylmethane; hydrogen fluoride; ethylmagnesium bromide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; p-toluenesulfonyl chloride; pyridinium chlorochromate; calcium carbonate; lithium chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(01)96657-8

Reference yield:

(2E,6E,1'S*,4'S*)-7-(4'-hydroxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl acetate (99477-55-1,99529-54-1,99529-56-3,99529-57-4) → Ascofuranone (38462-04-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 5.14 g / 14 h / 80 °C

2: 76.3 percent / Et₃N, HSiCl₃ / benzene / 96 h / Ambient temperature

3: imidazole / dimethylformamide / 6 h / Ambient temperature

4: 92.9 percent / K₂CO₃ / methanol; H₂O / 48 h / Ambient temperature

5: 1.26 g / n-BuLi, Ph₃CH, p-TsCl, LiCl / diethyl ether; hexamethylphosphoric acid triamide; hexane / 0.42 h / 0 °C

6: n-BuLi, HMPA / tetrahydrofuran; hexane / 0.75 h / -70 °C

7: 50.2 percent / CaCO₃, NCS / H₂O; dimethylformamide / Ambient temperature

8: 57 percent / DBU / tetrahydrofuran / 6 h / Heating

9: 1) EtMgBr / 1) ether, room temp., 1 h. 10 min.; 2) ether evaporated; 100 degC, 10 min.

10: 71 percent / HF / acetonitrile; H₂O / 1 h / Ambient temperature

11: 22.2 percent / pyridinium chlorochromate / CH₂Cl₂ / 3 h / Ambient temperature

With 1H-imidazole; N,N,N,N,N,N-hexamethylphosphoric triamide; N-chloro-succinimide; n-butyllithium; triphenylmethane; trichlorosilane; hydrogen fluoride; ethylmagnesium bromide; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; p-toluenesulfonyl chloride; pyridinium chlorochromate; calcium carbonate; lithium chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; benzene;

DOI:10.1016/S0040-4020(01)96657-8

upstream raw materials:

(1''S,4''S)-(-)-ascofuranol

(2E,6E,1'S,4'S)-(+)-7-(4'-hydroxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl acetate

(2E,6E,1'S*,4'S*)-7-(4'-hydroxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadienyl acetate

(2E,6E,1'S,4'S)-(+)-7-(4'-t-butyldimethylsilyloxy-3',3'-dimethyl-2'-oxacyclopentyl)-3,7-dimethyl-2,6-heptadien-1-ol

Downstream raw materials:

3-chloro-4,6-dihydroxy-2-methyl-5-[3-methyl-7-(tetrahydro-5,5-dimethyl-4-oxo-2-furanyl)octyl]-benzaldehyde

4-O-Acetyl-2-O-methyl-ascofuranone

4-O-Acetyl-ascofuranone

Refernces