benzoic acid 5-[(3'S,5'R)-2'-(tert-butyldimethylsilanyloxymethyl)-3'-(2'',2''-dimethylpropionyloxymethyl)-5'-(4''-methoxybenzyloxy)cyclopent-1'-enyl]pentyl ester

Base Information

• Chemical Name: benzoic acid 5-[(3'S,5'R)-2'-(tert-butyldimethylsilanyloxymethyl)-3'-(2'',2''-dimethylpropionyloxymethyl)-5'-(4''-methoxybenzyloxy)cyclopent-1'-enyl]pentyl ester
• CAS No.: 896110-34-2
• Molecular Formula: C₃₈H₅₆O₇Si
• Molecular Weight: 652.944
• Mol file: 896110-34-2.mol

Synonyms:

Chemical Property of benzoic acid 5-[(3'S,5'R)-2'-(tert-butyldimethylsilanyloxymethyl)-3'-(2'',2''-dimethylpropionyloxymethyl)-5'-(4''-methoxybenzyloxy)cyclopent-1'-enyl]pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzoic acid 5-[(3'S,5'R)-2'-(tert-butyldimethylsilanyloxymethyl)-3'-(2'',2''-dimethylpropionyloxymethyl)-5'-(4''-methoxybenzyloxy)cyclopent-1'-enyl]pentyl ester

There total 7 articles about benzoic acid 5-[(3'S,5'R)-2'-(tert-butyldimethylsilanyloxymethyl)-3'-(2'',2''-dimethylpropionyloxymethyl)-5'-(4''-methoxybenzyloxy)cyclopent-1'-enyl]pentyl 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:

Benzoic acid 5-[(3S,5R)-3-(2,2-dimethyl-propionyloxymethyl)-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-cyclopent-1-enyl]-pentyl ester (896110-61-5) + tert-butyldimethylsilyl chloride (18162-48-6) → benzoic acid 5-[(3'S,5'R)-2'-(tert-butyldimethylsilanyloxymethyl)-3'-(2'',2''-dimethylpropionyloxymethyl)-5'-(4''-methoxybenzyloxy)cyclopent-1'-enyl]pentyl ester (896110-34-2)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2005.11.096

Reference yield:

benzoic acid 5-[(R)-4'-(2'',2''-dimethylpropionyloxymethyl)-6'-oxocyclohex-1'-enyl]pentyl ester (896110-29-5) → benzoic acid 5-[(3'S,5'R)-2'-(tert-butyldimethylsilanyloxymethyl)-3'-(2'',2''-dimethylpropionyloxymethyl)-5'-(4''-methoxybenzyloxy)cyclopent-1'-enyl]pentyl ester (896110-34-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: CeCl₃*7H₂O; NaBH₄ / methanol / 1 h / 0 °C

2.1: TfOH / diethyl ether / 0 - 20 °C

3.1: ozone / CH₂Cl₂; methanol / -78 °C

3.2: PPh₃ / CH₂Cl₂; methanol / -78 - 20 °C

4.1: piperidine; acetic acid / diethyl ether / 20 h / Heating

5.1: NaBH₄ / methanol / 0.33 h / 0 °C

6.1: imidazole / CH₂Cl₂ / 1 h / 20 °C

With piperidine; 1H-imidazole; sodium tetrahydroborate; cerium(III) chloride; trifluorormethanesulfonic acid; ozone; acetic acid; In methanol; diethyl ether; dichloromethane; 1.1: Luche reaction;

DOI:10.1016/j.tet.2005.11.096

Reference yield:

Benzoic acid 5-[(R)-4-(2,2-dimethyl-propionyloxymethyl)-6-hydroxy-cyclohex-1-enyl]-pentyl ester → benzoic acid 5-[(3'S,5'R)-2'-(tert-butyldimethylsilanyloxymethyl)-3'-(2'',2''-dimethylpropionyloxymethyl)-5'-(4''-methoxybenzyloxy)cyclopent-1'-enyl]pentyl ester (896110-34-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: TfOH / diethyl ether / 0 - 20 °C

2.1: ozone / CH₂Cl₂; methanol / -78 °C

2.2: PPh₃ / CH₂Cl₂; methanol / -78 - 20 °C

3.1: piperidine; acetic acid / diethyl ether / 20 h / Heating

4.1: NaBH₄ / methanol / 0.33 h / 0 °C

5.1: imidazole / CH₂Cl₂ / 1 h / 20 °C

With piperidine; 1H-imidazole; sodium tetrahydroborate; trifluorormethanesulfonic acid; ozone; acetic acid; In methanol; diethyl ether; dichloromethane;

DOI:10.1016/j.tet.2005.11.096

upstream raw materials:

Benzoic acid 5-[(3S,5R)-3-(2,2-dimethyl-propionyloxymethyl)-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-cyclopent-1-enyl]-pentyl ester

tert-butyldimethylsilyl chloride

benzoic acid 5-[(R)-4'-(2'',2''-dimethylpropionyloxymethyl)-6'-oxocyclohex-1'-enyl]pentyl ester

benzoic acid 5-[(4'R,6'R)-4'-(2'',2''-dimethylpropionyloxymethyl)-6'-(4''-methoxybenzyloxy)cyclohex-1'-enyl]pentyl ester

Downstream raw materials:

2,2-Dimethyl-propionic acid (1S,4R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-(5-hydroxy-pentyl)-4-(4-methoxy-benzyloxy)-cyclopent-2-enylmethyl ester

2,2-dimethylpropionic acid [(1S,4R)-2-(tert-butyldimethylsilanyloxymethyl)-4-(4'-methoxybenzyloxy)-3-[5-(2'-methoxyethoxymethoxy)pentyl]cyclopent-2-enyl]methyl ester