5-Heptenoic acid,7-[5-oxo-3-[(triethylsilyl)oxy]-1-cyclopenten-1-yl]-,Methyl ester,(5Z)-

Base Information

• Chemical Name: 5-Heptenoic acid,7-[5-oxo-3-[(triethylsilyl)oxy]-1-cyclopenten-1-yl]-,Methyl ester,(5Z)-
• CAS No.: 102494-28-0
• Molecular Formula: C19H32O4Si
• Molecular Weight: 352.54000
• Mol file: 102494-28-0.mol

Synonyms:5-Heptenoic acid, 7-[5-oxo-3-[(triethylsilyl)oxy]-1-cyclopenten-1-yl]-, methyl ester, (Z)- (9CI);5-Heptenoic acid, 7-[5-oxo-3-[(triethylsilyl)oxy]-1-cyclopenten-1-yl]-, methyl ester, (Z)-(±)-;

Chemical Property of 5-Heptenoic acid,7-[5-oxo-3-[(triethylsilyl)oxy]-1-cyclopenten-1-yl]-,Methyl ester,(5Z)-

Chemical Property:

• PSA: 52.60000
• LogP: 4.56560
• Storage Temp.: 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

(Z)-Methyl 7-(5-oxo-3-((triethylsilyl)-oxy)cyclopent-1-en-1-yl)hept-5-enoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-Heptenoic acid,7-[5-oxo-3-[(triethylsilyl)oxy]-1-cyclopenten-1-yl]-,Methyl ester,(5Z)-

There total 1 articles about 5-Heptenoic acid,7-[5-oxo-3-[(triethylsilyl)oxy]-1-cyclopenten-1-yl]-,Methyl ester,(5Z)- 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:

triethylsilyl chloride (994-30-9) + methyl 7-(3-hydroxy-5-oxo-1-cyclopenten-1-yl)-5(Z)-heptenoate (54594-85-3) → (+/-)-methyl 7-<3-<(triethylsilyl)oxy>-5-oxo-1-cyclopenten-1-yl>-5(Z)-heptenoate (102494-28-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 1h; Ambient temperature;

DOI:10.1021/jm00157a013

Reference yield:

(+/-)-methyl 7-<3-<(triethylsilyl)oxy>-5-oxo-1-cyclopenten-1-yl>-5(Z)-heptenoate (102494-28-0) → (+/-)-methyl 9-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-16-methyl-2-(phenylseleno)-11α-<(triethylsilyl)oxy>-16-<(trimethylsilyl)oxy>prosta-5(Z),8,13(E)-trien-1-oate

Guidance literature:

Multi-step reaction with 2 steps

1: 2.) hexamethylphosphoric triamide (HMPT) / 1.) ether, -60 deg C, 1 h, 2.) ether, -20 deg C, 1 h

2: 90 percent / N-isopropylcyclohexylamine,n-BuLi / tetrahydrofuran / -60 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; N-cyclohexylisopropylamine; In tetrahydrofuran;

DOI:10.1021/jm00157a013

Reference yield:

(+/-)-methyl 7-<3-<(triethylsilyl)oxy>-5-oxo-1-cyclopenten-1-yl>-5(Z)-heptenoate (102494-28-0) → (+/-)-15-deoxy-16-methyl-16-hydroxy-3(E)-didehydroprostaglandin E2 methyl ester (81834-82-4,81834-83-5,81834-84-6,81834-85-7,81834-90-4,81834-91-5,81834-92-6,81834-93-7,81834-96-0,81834-97-1,81873-58-7,81873-59-8,112137-92-5,112137-93-6,112244-30-1,119239-56-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 2.) hexamethylphosphoric triamide (HMPT) / 1.) ether, -60 deg C, 1 h, 2.) ether, -20 deg C, 1 h

2: 90 percent / N-isopropylcyclohexylamine,n-BuLi / tetrahydrofuran / -60 °C

3: 40 percent / 30percent H₂O₂, pyridine / CH₂Cl₂; H₂O / 4 h / Ambient temperature

4: N-isopropylcyclohexylamine, N-BuLi, hexamethylphosphoric triamide (HMPT) / tetrahydrofuran

5: AcOH / tetrahydrofuran; H₂O / 24 h / Ambient temperature

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; N-cyclohexylisopropylamine; dihydrogen peroxide; acetic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jm00157a013

upstream raw materials:

triethylsilyl chloride

methyl 7-(3-hydroxy-5-oxo-1-cyclopenten-1-yl)-5(Z)-heptenoate

Downstream raw materials:

(+/-)-15-deoxy-16-methyl-16-hydroxy-3(E)-didehydroprostaglandin E₂ methyl ester

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