(Z)-7-[(1R,2S,5R)-2-(2-Hydroxy-ethyl)-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid methyl ester

Base Information

• Chemical Name: (Z)-7-[(1R,2S,5R)-2-(2-Hydroxy-ethyl)-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid methyl ester
• CAS No.: 913617-89-7
• Molecular Formula: C₂₃H₃₂O₅
• Molecular Weight: 388.504
• Mol file: 913617-89-7.mol

Synonyms:(Z)-7-[(1R,2S,5R)-2-(2-Hydroxy-ethyl)-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid methyl ester

Chemical Property of (Z)-7-[(1R,2S,5R)-2-(2-Hydroxy-ethyl)-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-7-[(1R,2S,5R)-2-(2-Hydroxy-ethyl)-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid methyl ester

There total 14 articles about (Z)-7-[(1R,2S,5R)-2-(2-Hydroxy-ethyl)-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid methyl 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: 99.0%

7-[2-[2-(tert-butyldiphenylsilanyloxy)ethyl]-5-(4-methoxybenzyloxy)-3-cyclopentenyl]-5-heptenoic acid methyl ester (913617-83-1) → (Z)-7-[(1R,2S,5R)-2-(2-Hydroxy-ethyl)-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid methyl ester (913617-89-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1016/j.tet.2006.08.068

Reference yield:

(4R)-4-vinyltetrahydropyran-2-one (913617-64-8) → (Z)-7-[(1R,2S,5R)-2-(2-Hydroxy-ethyl)-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid methyl ester (913617-89-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: dibutylboron trifluoromethane sulfonate; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 °C

1.2: 80 percent / CH₂Cl₂ / 1 h / -78 °C

2.1: camphorsulfonic acid / CH₂Cl₂; cyclohexane / 24 h / 20 °C

3.1: 839.5 mg / LiAlH₄ / diethyl ether / 2 h / 20 °C

4.1: 78 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / toluene / 1.5 h / 50 °C

5.1: 53 percent / imidazole / dimethylformamide / 1 h / 0 °C

6.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

7.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / 20 °C

8.1: 127 mg / p-toluenesulfonic acid / acetone / 1 h / 20 °C

9.1: 76 percent / NaHMDS / tetrahydrofuran / 1 h / 20 °C

10.1: 90 percent / diethyl ether / 0.25 h / 0 °C

11.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone; toluene; 1.1: Mukaiyama aldol reaction / 1.2: Mukaiyama aldol reaction / 7.1: Wittig reaction / 9.1: Wittig reaction;

DOI:10.1016/j.tet.2006.08.068

Reference yield:

(R)-3-(2-Hydroxy-ethyl)-pent-4-enoic acid → (Z)-7-[(1R,2S,5R)-2-(2-Hydroxy-ethyl)-5-(4-methoxy-benzyloxy)-cyclopent-3-enyl]-hept-5-enoic acid methyl ester (913617-89-7)

Guidance literature:

Multi-step reaction with 12 steps

1.1: 1.54 g / camphorsulfonic acid / benzene / 15 h / Heating

2.1: dibutylboron trifluoromethane sulfonate; diisopropylethylamine / CH₂Cl₂ / 2 h / -78 °C

2.2: 80 percent / CH₂Cl₂ / 1 h / -78 °C

3.1: camphorsulfonic acid / CH₂Cl₂; cyclohexane / 24 h / 20 °C

4.1: 839.5 mg / LiAlH₄ / diethyl ether / 2 h / 20 °C

5.1: 78 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / toluene / 1.5 h / 50 °C

6.1: 53 percent / imidazole / dimethylformamide / 1 h / 0 °C

7.1: 95 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.5 h / 20 °C

8.1: n-butyllithium / hexane; tetrahydrofuran / 2 h / 20 °C

9.1: 127 mg / p-toluenesulfonic acid / acetone / 1 h / 20 °C

10.1: 76 percent / NaHMDS / tetrahydrofuran / 1 h / 20 °C

11.1: 90 percent / diethyl ether / 0.25 h / 0 °C

12.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

With 1H-imidazole; lithium aluminium tetrahydride; n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; Dess-Martin periodane; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; Grubbs catalyst first generation; camphor-10-sulfonic acid; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; cyclohexane; N,N-dimethyl-formamide; acetone; toluene; benzene; 2.1: Mukaiyama aldol reaction / 2.2: Mukaiyama aldol reaction / 8.1: Wittig reaction / 10.1: Wittig reaction;

DOI:10.1016/j.tet.2006.08.068

upstream raw materials:

7-[2-[2-(tert-butyldiphenylsilanyloxy)ethyl]-5-(4-methoxybenzyloxy)-3-cyclopentenyl]-5-heptenoic acid methyl ester

(4R)-4-vinyltetrahydropyran-2-one

3-(1-hydroxy-2-propenyl)-4-vinyltetrahydropyran-2-one

3-(2-hydroxyethyl)-4-pentenoic acid (1-phenylethyl) amide

Downstream raw materials:

7-[2-(4-methoxybenzyloxy)-5-(2-octenyl)cyclopent-3-enyl]-5-heptenoic acid methyl ester

(Z)-7-[(1R,2R,5S)-2-(4-Methoxy-benzyloxy)-5-(2-oxo-ethyl)-cyclopent-3-enyl]-hept-5-enoic acid methyl ester