7-[(3R)-3-[[(1,1-diMethylethyl)diMethylsilyl]oxy]-5-oxo-1-cyclopenten-1-yl]-(5Z)-Heptenoic acid-1-Methylethyl ester

Base Information

• Chemical Name: 7-[(3R)-3-[[(1,1-diMethylethyl)diMethylsilyl]oxy]-5-oxo-1-cyclopenten-1-yl]-(5Z)-Heptenoic acid-1-Methylethyl ester
• CAS No.: 474944-36-0
• Molecular Formula: C21H36O4Si
• Molecular Weight: 380.6
• Mol file: 474944-36-0.mol

Synonyms:isopropyl (3R,Z)-7-(3-(tert-butyldimethylsilyloxy)-5-oxo-cyclopent-1-enyl)-hept-5-enoate;isopropyl (3R,Z)-7-(3-(tert-butyldimethylsilyloxy)-5-oxo-cyclopent-1-en-1-yl)-hept-5-enoate;isopropyl (Z)-7-[(3R)-3-(tertbutyldimethylsilanyloxy)-5-oxocyclopent-1-enyl]hept-5-enoate;

Chemical Property of 7-[(3R)-3-[[(1,1-diMethylethyl)diMethylsilyl]oxy]-5-oxo-1-cyclopenten-1-yl]-(5Z)-Heptenoic acid-1-Methylethyl ester

Chemical Property:

• PSA: 52.60000
• LogP: 5.34420

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 7-[(3R)-3-[[(1,1-diMethylethyl)diMethylsilyl]oxy]-5-oxo-1-cyclopenten-1-yl]-(5Z)-Heptenoic acid-1-Methylethyl ester

There total 4 articles about 7-[(3R)-3-[[(1,1-diMethylethyl)diMethylsilyl]oxy]-5-oxo-1-cyclopenten-1-yl]-(5Z)-Heptenoic acid-1-Methylethyl 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: 82.0%

isopropyl (3R,Z)-7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-hept-5-enoate (876953-80-9) + tert-butyldimethylsilyl chloride (18162-48-6) → (Z)-7-[(3R)-3-(tert-butyldimethylsilanyloxy)-5-oxo-cyclopent-1-enyl]hept-5-enoic acid isopropyl ester (474944-36-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; Large scale;

DOI:10.1021/op300188x

Reference yield:

isopropyl (3S,Z)-7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-hept-5-enoate (876953-71-8) → (Z)-7-[(3R)-3-(tert-butyldimethylsilanyloxy)-5-oxo-cyclopent-1-enyl]hept-5-enoic acid isopropyl ester (474944-36-0)

Guidance literature:

Multi-step reaction with 3 steps

1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran / 5.5 h / 0 - 20 °C

2: guanidine nitrate / methanol / 0 - 10 °C

3: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Large scale

With 1H-imidazole; guanidine nitrate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1021/op300188x

Reference yield:

(3R,Z)-7-(3-acetoxy-5-oxocyclopent-1-en-1-yl)-hept-5-enoate (1190883-13-6) → (Z)-7-[(3R)-3-(tert-butyldimethylsilanyloxy)-5-oxo-cyclopent-1-enyl]hept-5-enoic acid isopropyl ester (474944-36-0)

Guidance literature:

Multi-step reaction with 2 steps

1: guanidine nitrate / methanol / 0 - 10 °C / Large scale

2: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Large scale

With 1H-imidazole; guanidine nitrate; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/op300188x

upstream raw materials:

isopropyl (3R,Z)-7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-hept-5-enoate

tert-butyldimethylsilyl chloride

isopropyl (3S,Z)-7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)-hept-5-enoate

(3R,Z)-7-(3-acetoxy-5-oxocyclopent-1-en-1-yl)-hept-5-enoate

Downstream raw materials:

(Z)-7-((1R,2R,3R)-3-[(tert-butyldimethylsilanyl)oxy]-2-{(E)-3-[(tert-butyldimethylsilanyl)oxy]-5-phenylpent-1-en-1-yl}-5-oxo-cyclopentyl)hept-5-enoic acid isopropyl ester

(Z)-7-((1R,2R,3R)-3-[(tert-butyldimethylsilanyl)oxy]2-((E)-3-((tert-butyldimethylsilanyl)oxy)-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)-5-oxo-cyclopentyl)hept-5-enoic acid isopropyl ester

Refernces

• 1、 -. "Process for the Preparation of Prostaglandin Analogues and Intermediates Thereof". Page/Page column 15. . Retrieved 2009/10/21.