(1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-15-(ethenyl)-1-quinquecyclopropanemethyl 3-ethenylbenzoate

Base Information

• Chemical Name: (1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-15-(ethenyl)-1-quinquecyclopropanemethyl 3-ethenylbenzoate
• CAS No.: 335248-52-7
• Molecular Formula: C₂₇H₃₂O₂
• Molecular Weight: 388.55
• Mol file: 335248-52-7.mol

Synonyms:(1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-15-(ethenyl)-1-quinquecyclopropanemethyl 3-ethenylbenzoate

Chemical Property of (1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-15-(ethenyl)-1-quinquecyclopropanemethyl 3-ethenylbenzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-15-(ethenyl)-1-quinquecyclopropanemethyl 3-ethenylbenzoate

There total 3 articles about (1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-15-(ethenyl)-1-quinquecyclopropanemethyl 3-ethenylbenzoate 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: 67.0%

3-vinylbenzoic acid (28447-20-3) + ((1S,2R,1'R,2'R,1''R,2''R,1'''R,2'''R,1''''R,2''''S)-2''''-Vinyl-[1,2';1',1'';2'',1''';2''',1'''']quinquecyclopropan-2-yl)-methanol (335248-50-5) → (1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-15-(ethenyl)-1-quinquecyclopropanemethyl 3-ethenylbenzoate (335248-52-7)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃;

DOI:10.1021/jo001167d

Reference yield:

(1S,2R,1'R,2'R,1''R,2''R,1'''R,2'''R,1''''S,2''''R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-[1,2';1',1'';2'',1''';2''',1'''']quinquecyclopropane-2''''-carbaldehyde → (1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-15-(ethenyl)-1-quinquecyclopropanemethyl 3-ethenylbenzoate (335248-52-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 mg / tetrahydrofuran / 1 h / 20 °C

2: 97 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

3: 67 percent / DCC; DMAP / CH₂Cl₂ / 20 °C

With dmap; tetrabutyl ammonium fluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 3: Steglich esterification;

DOI:10.1021/jo001167d

Reference yield:

(1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-1-[(tert-butyldimethylsilyloxy)methyl]-15-ethenyl-quinquecyclopropane (335248-49-2) → (1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-15-(ethenyl)-1-quinquecyclopropanemethyl 3-ethenylbenzoate (335248-52-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 97 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

2: 67 percent / DCC; DMAP / CH₂Cl₂ / 20 °C

With dmap; tetrabutyl ammonium fluoride; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 2: Steglich esterification;

DOI:10.1021/jo001167d

upstream raw materials:

3-vinylbenzoic acid

((1S,2R,1'R,2'R,1''R,2''R,1'''R,2'''R,1''''R,2''''S)-2''''-Vinyl-[1,2';1',1'';2'',1''';2''',1'''']quinquecyclopropan-2-yl)-methanol

(1R,3S,4R,6S,7R,9S,10R,12S,13R,15S)-1-[(tert-butyldimethylsilyloxy)methyl]-15-ethenyl-quinquecyclopropane