10-Methoxy-1,4,14,18,18-pentamethyl-2,7-dioxapentacyclo[11.8.0.03,11.05,9.014,19]henicosa-3(11),4,9-triene-8,17-dione

Base Information

• Chemical Name: 10-Methoxy-1,4,14,18,18-pentamethyl-2,7-dioxapentacyclo[11.8.0.03,11.05,9.014,19]henicosa-3(11),4,9-triene-8,17-dione
• CAS No.: 87833-53-2
• Molecular Formula: C₂₅H₃₂O₅
• Molecular Weight: 412.526
• Wikidata: Q105125143
• Mol file: 87833-53-2.mol

Synonyms:

Chemical Property of 10-Methoxy-1,4,14,18,18-pentamethyl-2,7-dioxapentacyclo[11.8.0.03,11.05,9.014,19]henicosa-3(11),4,9-triene-8,17-dione

Chemical Property:

• Vapor Pressure: 7.15E-14mmHg at 25°C
• Boiling Point: 589.5°C at 760 mmHg
• Flash Point: 313.9°C
• Density: 1.17g/cm³
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 412.22497412
• Heavy Atom Count: 30
• Complexity: 761

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=C2COC(=O)C2=C(C3=C1OC4(CCC5C(C(=O)CCC5(C4C3)C)(C)C)C)OC

Technology Process of 10-Methoxy-1,4,14,18,18-pentamethyl-2,7-dioxapentacyclo[11.8.0.03,11.05,9.014,19]henicosa-3(11),4,9-triene-8,17-dione

There total 14 articles about 10-Methoxy-1,4,14,18,18-pentamethyl-2,7-dioxapentacyclo[11.8.0.03,11.05,9.014,19]henicosa-3(11),4,9-triene-8,17-dione 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: 83.0%

(3S,4aR,6aS,13aR,13bS)-3-Hydroxy-12-methoxy-4,4,6a,8,13b-pentamethyl-1,2,3,4,4a,5,6,6a,9,13,13a,13b-dodecahydro-11H-benzo[a]furo[3,4-i]-xanthen-11-one → austalide K (87833-53-2)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 25 ℃; for 1h;

DOI:10.1021/acs.joc.9b00142

Reference yield:

(3S,4aR,6aS,13aR,13bS)-12-methoxy-4,4,13b-trimethyl-11-oxo-6a-((phenylselanyl)methyl)-1,3,4,4a,5,6,6a,9,11,13,13a,13b-dodecahydro-2H-benzo[a]furo[3,4-i]xanthen-3-yl acetate → austalide K (87833-53-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 5 h / 100 °C / Inert atmosphere; Schlenk technique

2: N-Bromosuccinimide; sulfuric acid / tetrahydrofuran / 17 h / 25 °C

3: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran; water / 18 h / 80 °C

4: magnesium / tetrahydrofuran; methanol / 21 h / 25 - 90 °C

5: Dess-Martin periodane / dichloromethane / 1 h / 25 °C

With N-Bromosuccinimide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; 2,2'-azobis(isobutyronitrile); sulfuric acid; tri-n-butyl-tin hydride; caesium carbonate; Dess-Martin periodane; magnesium; In tetrahydrofuran; methanol; dichloromethane; water; benzene; 3: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.joc.9b00142

Reference yield:

(3S,4aR,6aS,13aR,13bS)-12-Methoxy-4,4,6a,13b-tetramethyl-11-oxo-1,3,4,4a,5,6,6a,9,11,13,13a,13b-dodecahydro-2H-benzo[a]furo[3,4-i]xanthen-3-yl acetate → austalide K (87833-53-2)

Guidance literature:

Multi-step reaction with 4 steps

1: N-Bromosuccinimide; sulfuric acid / tetrahydrofuran / 17 h / 25 °C

2: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran; water / 18 h / 80 °C

3: magnesium / tetrahydrofuran; methanol / 21 h / 25 - 90 °C

4: Dess-Martin periodane / dichloromethane / 1 h / 25 °C

With N-Bromosuccinimide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sulfuric acid; caesium carbonate; Dess-Martin periodane; magnesium; In tetrahydrofuran; methanol; dichloromethane; water; 2: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.joc.9b00142