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

Base Information

• Chemical Name: (R)-Methyl 7-(3-((tert-butyldimethylsilyl)oxy)-5-oxocyclopent-1-en-1-yl)heptanoate
• CAS No.: 41138-69-6
• Molecular Formula: C19H34O4Si
• Molecular Weight: 354.562
• DSSTox Substance ID: DTXSID50452358
• Nikkaji Number: J991.219C
• Wikidata: Q72490947
• Mol file: 41138-69-6.mol

Synonyms:41138-69-6;(R)-Methyl 7-(3-((tert-butyldimethylsilyl)oxy)-5-oxocyclopent-1-en-1-yl)heptanoate;Methyl (R)-(+)-3-(tert-butyldimethylsilyloxy)-5-oxo-1-cyclopentene-1-heptanoate;methyl 7-[(3R)-3-[tert-butyl(dimethyl)silyl]oxy-5-oxocyclopenten-1-yl]heptanoate;(R)-Methyl 7-(3-((tert-butyldimethylsilyl)-oxy)-5-oxocyclopent-1-en-1-yl)heptanoate;SCHEMBL4021195;DTXSID50452358;Methyl(R)-(+)-3-(tert-butyldimethylsilyloxy)-5-oxo-1-cyclopentene-1-heptanoate;NIOJULSEJPAEJV-INIZCTEOSA-N;(R)-methyl 7-(3-(tert-butyldimethylsilyloxy)-5-oxocyclopent-1-enyl)heptanoate;AKOS016009637;AC-28152;MS-21569;A854976;J-504553;(3R)-3alpha-(tert-Butyldimethylsiloxy)-5-oxo-1-cyclopentene-1-heptanoic acid methyl ester;(R)-Methyl 7-(3-((Tert-Butyldimethylsilyl)-Oxy)-5-Oxcyclopent-1-En-1-Yl)Heptanoate;(R)-Methyl 7-(3-((Tert-Butyldimethylsilyl)Oxy)-5-Oxcyclopent-1-En-1-Yl)Heptanoate;(R)4-TERT-BUTYLDIMETHYLSILYLOXY-2-(6-CARBOMETHOXYHEXYL)-CYCLOPENT-2-ENONE;Methyl 7-[(3R)-3-{[tert-butyl(dimethyl)silyl]oxy}-5-oxocyclopent-1-en-1-yl]heptanoate;1-Cyclopentene-1-heptanoic acid,3-[[1,1-dimethylethyl)dimethylsilyl]oxy]-5-oxo-,methyl ester, (3R)-

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

Chemical Property:

• Vapor Pressure: 8.89E-07mmHg at 25°C
• Refractive Index: n20/D 1.467(lit.)
• Boiling Point: 405.2 ºC at 760 mmHg
• Flash Point: 165.2 ºC
• PSA: 52.60000
• Density: 0.98 g/cm³
• 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:

98%,99%, ^*data from raw suppliers

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

Safty Information:

• Statements: 10
• Safety Statements: 16

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1CC(=O)C(=C1)CCCCCCC(=O)OC
• Isomeric SMILES: CC(C)(C)[Si](C)(C)O[C@@H]1CC(=O)C(=C1)CCCCCCC(=O)OC

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

There total 11 articles about (R)-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: 98.0%

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone (41138-61-8) + tert-butyldimethylsilyl chloride (18162-48-6) → 7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester (41138-69-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

Reference yield: 89.0%

(4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone (41138-61-8) + t-butyldimethylsiyl triflate (69739-34-0) → 7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester (41138-69-6)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -78 - 20 ℃; for 15h;

DOI:10.1021/jm990542v

Reference yield: 74.0%

methyl hept-6-enoate (1745-17-1) + (R)-4-((tert-butyldimethylsilyl)oxy)-2-iodocyclopent-2-en-1-one (150686-70-7) → 7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester (41138-69-6)

Guidance literature:

With 9-borabicyclo[3.3.1]nonane dimer; water; caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 ℃;

DOI:10.1039/a903813b

upstream raw materials:

methyl hept-6-enoate

(R)-4-((tert-butyldimethylsilyl)oxy)-2-iodocyclopent-2-en-1-one

C₇H₁₃IO₂Zn

(3S,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-2-methylene-cyclopentanone

Downstream raw materials:

7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester

7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-ethoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester

7-(3-(tert-butyl-dimethyl-silanyloxy)-2-{3-(tert-butyl-dimethyl-silanyloxy)-4-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-but-1-enyl}-5-oxo-cyclopentyl)-heptanoic acid methyl ester

prostaglandin E₁ methyl ester

Refernces

• 1、 -. "AROMATIC C 16?-C 20?-SUBSTITUTED TETRAHYDRO PROSTAGLANDINS USEFUL AS FP AGONISTS". Page/Page column 9. . Retrieved 2010/02/07.
• 2、 Wang, Yili,Wos, John A.,Dirr, Michelle J.,Soper, David L.,DeLong, Mitchell A.,Mieling, Glen E.,De, Biswanath,Amburgey, Jack S.,Suchanek, Eric G.,Taylor, Cynthia J.. "Design and synthesis of 13,14-dihydro prostaglandin F(1α) analogues as potent and selective ligands for the human FP receptor". . p. 945 - 952. Retrieved 2007/10/03.