3α-acetoxy-14-(benzoyloxy)-13-nortrichothec-9-en-12-one

Base Information

• Chemical Name: 3α-acetoxy-14-(benzoyloxy)-13-nortrichothec-9-en-12-one
• CAS No.: 101933-71-5
• Molecular Formula: C₂₃H₂₆O₆
• Molecular Weight: 398.456
• Mol file: 101933-71-5.mol

Synonyms:3α-acetoxy-14-(benzoyloxy)-13-nortrichothec-9-en-12-one

Chemical Property of 3α-acetoxy-14-(benzoyloxy)-13-nortrichothec-9-en-12-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3α-acetoxy-14-(benzoyloxy)-13-nortrichothec-9-en-12-one

There total 8 articles about 3α-acetoxy-14-(benzoyloxy)-13-nortrichothec-9-en-12-one 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: 85.0%

3α-acetoxy-14-(benzoyloxy)-12β-hydroxy-13-nortrichothec-9-ene (101933-70-4) → 3α-acetoxy-14-(benzoyloxy)-13-nortrichothec-9-en-12-one (101933-71-5)

Guidance literature:

With Collins oxidation agent; In dichloromethane; for 1h; Ambient temperature;

DOI:10.1021/jo00361a001

Reference yield:

3α,4α-dihydroxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-hydroxy-4-methylcyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane (101933-65-7) → 3α-acetoxy-14-(benzoyloxy)-13-nortrichothec-9-en-12-one (101933-71-5)

Guidance literature:

Multi-step reaction with 4 steps

1: p-toluenesulfonic acid / CH₂Cl₂ / 2 h / Ambient temperature

2: 84 percent / pyridine / 17 h / Ambient temperature

3: 1 M n-bitulammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

4: 85 percent / Collins reagent / CH₂Cl₂ / 1 h / Ambient temperature

With Collins oxidation agent; n-bitulammonium fluoride; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1021/jo00361a001

Reference yield:

3α,4α-diacetoxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-oxocyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane (101933-52-2) → 3α-acetoxy-14-(benzoyloxy)-13-nortrichothec-9-en-12-one (101933-71-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 919 mg / diethyl ether; tetrahydrofuran / 2.5 h / -78 °C

2: 728 mg / potassium carbonate / methanol; H₂O / 2 h / Ambient temperature

3: p-toluenesulfonic acid / CH₂Cl₂ / 2 h / Ambient temperature

4: 84 percent / pyridine / 17 h / Ambient temperature

5: 1 M n-bitulammonium fluoride / tetrahydrofuran / 2 h / Ambient temperature

6: 85 percent / Collins reagent / CH₂Cl₂ / 1 h / Ambient temperature

With Collins oxidation agent; n-bitulammonium fluoride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; diethyl ether; dichloromethane; water;

DOI:10.1021/jo00361a001

upstream raw materials:

3α-acetoxy-14-(benzoyloxy)-12β-hydroxy-13-nortrichothec-9-ene

14-(benzyloxy)-12β-((tert-butyldimethylsilyl)oxy)-3α-hydroxy-13-nortrichothec-9-ene

Benzoic acid (1S,2R,7R,9S,10R,11R)-11-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-2,5-dimethyl-8-oxa-tricyclo[7.2.1.0^2,7]dodec-5-en-1-ylmethyl ester

3α,4α-dihydroxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-hydroxy-4-methylcyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane