Methyl 7-(3-((tert-butyldimethylsilyl)oxy)-5-oxocyclopent-1-en-1-yl)heptanoate

Base Information

• Chemical Name: Methyl 7-(3-((tert-butyldimethylsilyl)oxy)-5-oxocyclopent-1-en-1-yl)heptanoate
• CAS No.: 161978-56-9
• Molecular Formula: C19H34O4Si
• Molecular Weight: 354.55600
• DSSTox Substance ID: DTXSID60405279
• Mol file: 161978-56-9.mol

Synonyms:161978-56-9;Methyl 7-(3-((tert-butyldimethylsilyl)oxy)-5-oxocyclopent-1-en-1-yl)heptanoate;methyl 7-[3-[tert-butyl(dimethyl)silyl]oxy-5-oxocyclopenten-1-yl]heptanoate;1-Cyclopentene-1-heptanoic acid, 3-[[(1,1-diMethylethyl)diMethylsilyl]oxy]-5-oxo-, Methyl ester;NIOJULSEJPAEJV-UHFFFAOYSA-N;SCHEMBL4021198;DTXSID60405279;Methyl(R)-(+)-3-(tert-butyldimethylsilyloxy)-5-oxo-1-cyclopentene-1-heptanoate;AKOS016004155;AC-28147;MS-21627;A854974;A910835;J-504552;(+/-) methyl 7-(3-tert-butyldimethylsilyloxy-5-oxo-1-cyclopentenyl)heptanoate;Methyl 7-(3-((Tert-Butyldimethylsilyl)Oxy)-5-Oxcyclopent-1-En-1-Yl)Heptanoate;Methyl7-(3-((tert-butyldimethylsilyl)oxy)-5-oxocyclopent-1-en-1-yl)heptanoate;1-Cyclopentene-1-heptanoic acid,3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxo-,methyl ester

Chemical Property of Methyl 7-(3-((tert-butyldimethylsilyl)oxy)-5-oxocyclopent-1-en-1-yl)heptanoate

Chemical Property:

• Boiling Point: 405.2±45.0 °C(Predicted)
• PSA: 52.60000
• Density: 0.98±0.1 g/cm3(Predicted)
• LogP: 4.78960
• Storage Temp.: 2-8°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 11
• Exact Mass: 354.22263610
• Heavy Atom Count: 24
• Complexity: 474

Purity/Quality:

97% ^*data from raw suppliers

Methyl 7-(3-((tert-butyldimethylsilyl)oxy)-5-oxocyclopent-1-en-1-yl)heptanoate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1CC(=O)C(=C1)CCCCCCC(=O)OC

Technology Process of Methyl 7-(3-((tert-butyldimethylsilyl)oxy)-5-oxocyclopent-1-en-1-yl)heptanoate

There total 1 articles about Methyl 7-(3-((tert-butyldimethylsilyl)oxy)-5-oxocyclopent-1-en-1-yl)heptanoate 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:

1H-imidazole (288-32-4) + butyldimethylsilyl chloride (1000-50-6) + (4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone (41138-61-8) → methyl 7-(3-tert-butyldimethylsilyloxy-5-oxo-1-cyclopentenyl)heptanoate (161978-56-9)

Guidance literature:

In N-methyl-acetamide; Petroleum ether;

Reference yield:

methyl 7-(3-tert-butyldimethylsilyloxy-5-oxo-1-cyclopentenyl)heptanoate (161978-56-9) → 7-[(1S,2S,3S)-2-((E)-1-Benzenesulfinyl-oct-2-enyl)-3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-cyclopentyl]-heptanoic acid methyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) butyllithium, 2.) hexamethylphosphoric triamide (HMPA) / 1.) THF, from -78 to -45 deg C, 50 min, 2.) THF, -78 deg C, 5 min

2: 80 percent m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / -10 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; 3-chloro-benzenecarboperoxoic acid; In dichloromethane;

DOI:10.1246/bcsj.55.3043

Reference yield:

methyl 7-(3-tert-butyldimethylsilyloxy-5-oxo-1-cyclopentenyl)heptanoate (161978-56-9) → 15-α methyl prostaglandin E1 (3434-33-1,20993-69-5,20993-71-9,25140-28-7,26769-71-1,26771-29-9,39765-04-3,39765-15-6,39765-16-7,42048-99-7,47493-31-2,52390-74-6,56084-38-9,68296-24-2,77520-07-1,98048-19-2,116837-92-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) butyllithium, 2.) hexamethylphosphoric triamide (HMPA) / 1.) THF, from -78 to -45 deg C, 50 min, 2.) THF, -78 deg C, 5 min

2: 80 percent m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / -10 °C

3: trimethyl phosphite / methanol / 3 h / 0 °C

4: 8.5 mg / hydrofluoric acid / acetonitrile / 2 h / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; hydrogen fluoride; 3-chloro-benzenecarboperoxoic acid; phosphorous acid trimethyl ester; In methanol; dichloromethane; acetonitrile;

DOI:10.1246/bcsj.55.3043

upstream raw materials:

1H-imidazole

butyldimethylsilyl chloride

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone

Downstream raw materials:

7-[(1S,3S)-2-[1-Benzenesulfonyl-2-(2-pentyl-[1,3]dioxolan-2-yl)-ethyl]-3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-cyclopentyl]-heptanoic acid methyl ester

15-α methyl prostaglandin E₁

dl-15-Isoprostaglandin E(1)-methylester