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

Base Information

• Chemical Name: 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
• CAS No.: 101933-68-0
• Molecular Formula: C₂₇H₄₀O₅Si
• Molecular Weight: 472.697
• Mol file: 101933-68-0.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 4 articles about 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 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:

3α,4α-dihydroxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-hydroxy-4-methylcyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane (101933-65-7) → 14-(benzyloxy)-12β-((tert-butyldimethylsilyl)oxy)-3α-hydroxy-13-nortrichothec-9-ene (101933-66-8) + Benzoic acid (1S,2R,7R,9S,10R,11R)-11-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-2,5-dimethyl-8-oxa-tricyclo[7.2.1.02,7]dodec-5-en-1-ylmethyl ester (101933-68-0)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 0 ℃; for 0.5h;

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) → Benzoic acid (1S,2R,7R,9S,10R,11R)-11-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-2,5-dimethyl-8-oxa-tricyclo[7.2.1.02,7]dodec-5-en-1-ylmethyl ester (101933-68-0)

Guidance literature:

Multi-step reaction with 3 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 / 0.5 h / 0 °C

With potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water;

DOI:10.1021/jo00361a001

Reference yield:

3α,4α-diacetoxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-hydroxy-4-methylcyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane (101933-64-6) → Benzoic acid (1S,2R,7R,9S,10R,11R)-11-(tert-butyl-dimethyl-silanyloxy)-10-hydroxy-2,5-dimethyl-8-oxa-tricyclo[7.2.1.02,7]dodec-5-en-1-ylmethyl ester (101933-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 728 mg / potassium carbonate / methanol; H₂O / 2 h / Ambient temperature

2: p-toluenesulfonic acid / CH₂Cl₂ / 0.5 h / 0 °C

With potassium carbonate; toluene-4-sulfonic acid; In methanol; dichloromethane; water;

DOI:10.1021/jo00361a001

upstream raw materials:

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

3α,4α-diacetoxy-1β-((benzoyloxy)methyl)-1-(1-methyl-4-oxocyclohex-2-enyl)-2β-((tert-butyldimethylsilyl)oxy)cyclopentane

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

Downstream raw materials:

3α-acetoxy-14-(benzoyloxy)-12β-((tert-butyldimethylsilyl)oxy)-13-nortrichothec-9-ene

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

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

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