Aphadilactone C

Base Information

• Chemical Name: Aphadilactone C
• CAS No.: 1522004-70-1
• Molecular Formula: C40H52O8
• Molecular Weight: 660.84
• Mol file: 1522004-70-1.mol

Synonyms:Aphadilactone C

Chemical Property of Aphadilactone C

Chemical Property:

• PSA: 105.20000
• LogP: 8.03340

Purity/Quality:

99% ^*data from raw suppliers

AphadilactoneC 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Aphadilactone C

There total 10 articles about Aphadilactone C 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:

(S,E)-6-(6-(5,5-dimethyl-4-oxo-4,5-dihydrofuran-3-yl)-2-methylhepta-1,6-dien-1-yl)-4-methyl-5,6-dihydro-2H-pyran-2-one → aphadilactone A (1522004-66-5) + aphadilactone B (1522004-68-7) + aphadilactone C (1522004-70-1) + aphadilactone D (1522004-73-4)

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; In toluene; at 170 ℃; for 17h; Overall yield = 65 %; Overall yield = 42 mg; Inert atmosphere; Sealed tube;

DOI:10.1021/jo501117k

Reference yield:

(2S,6S)-2-((E)-2-iodoprop-1-en-1-yl)-6-isopropoxy-4-methyl-3,6-dihydro-2H-pyran (1615686-83-3) → aphadilactone A (1522004-66-5) + aphadilactone B (1522004-68-7) + aphadilactone C (1522004-70-1) + aphadilactone D (1522004-73-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: caesium carbonate; triphenyl-arsane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran; N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

3.1: dichloromethane / 0.17 h / 0 °C / Molecular sieve; Inert atmosphere

3.2: 2 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

4.1: triethylamine / dichloromethane / 10 h / 20 °C

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -40 °C

5.2: 2.17 h / -78 - -40 °C

6.1: pyridinium p-toluenesulfonate / acetone; water / 4 h / 20 °C

7.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C

8.1: toluene-4-sulfonic acid / dichloromethane / 3 h / 20 °C

9.1: 2,6-di-tert-butyl-4-methyl-phenol / toluene / 17 h / 170 °C / Inert atmosphere; Sealed tube

With manganese(IV) oxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; caesium carbonate; toluene-4-sulfonic acid; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 1.1: |Suzuki Coupling / 9.1: |Diels-Alder Cycloaddition;

DOI:10.1021/jo501117k

Reference yield:

tributyl((E)-1-((2S,6S)-6-isopropoxy-4-methyl-3,6-dihydro-2H-pyran-2-yl)prop-1-en-2-yl)stannane (1615686-82-2) → aphadilactone A (1522004-66-5) + aphadilactone B (1522004-68-7) + aphadilactone C (1522004-70-1) + aphadilactone D (1522004-73-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: N-iodo-succinimide / tetrahydrofuran / 0.33 h / -17 °C

2.1: caesium carbonate; triphenyl-arsane; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; tetrahydrofuran; N,N-dimethyl-formamide / 0.25 h / 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 6 h / 20 °C / Inert atmosphere

4.1: dichloromethane / 0.17 h / 0 °C / Molecular sieve; Inert atmosphere

4.2: 2 h / 0 - 20 °C / Molecular sieve; Inert atmosphere

5.1: triethylamine / dichloromethane / 10 h / 20 °C

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 3 h / -40 °C

6.2: 2.17 h / -78 - -40 °C

7.1: pyridinium p-toluenesulfonate / acetone; water / 4 h / 20 °C

8.1: manganese(IV) oxide / dichloromethane / 16 h / 20 °C

9.1: toluene-4-sulfonic acid / dichloromethane / 3 h / 20 °C

10.1: 2,6-di-tert-butyl-4-methyl-phenol / toluene / 17 h / 170 °C / Inert atmosphere; Sealed tube

With manganese(IV) oxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-iodo-succinimide; triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; caesium carbonate; toluene-4-sulfonic acid; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 2.1: |Suzuki Coupling / 10.1: |Diels-Alder Cycloaddition;

DOI:10.1021/jo501117k

upstream raw materials:

(2S,6S)-2-((E)-2-iodoprop-1-en-1-yl)-6-isopropoxy-4-methyl-3,6-dihydro-2H-pyran

tributyl((E)-1-((2S,6S)-6-isopropoxy-4-methyl-3,6-dihydro-2H-pyran-2-yl)prop-1-en-2-yl)stannane

tert-butyl(((E)-7-((2S,6S)-6-isopropoxy-4-methyl-3,6-dihydro-2H-pyran-2-yl)-6-methylhept-6-en-1-yl)oxy)dimethylsilane

(E)-7-((2S,6S)-6-isopropoxy-4-methyl-3,6-dihydro-2H-pyran-2-yl)-6-methylhept-6-en-1-ol

Refernces