118456-54-5

Basic information

• Product Name: (3R)-5-Oxo-3-[(triethylsilyl)oxy]-1-cyclopentene-1-heptanoic Acid Methyl Ester
• Synonyms: (3R)-5-Oxo-3-[(triethylsilyl)oxy]-1-cyclopentene-1-heptanoic Acid Methyl Ester;(3R)-5-Oxo-3-[(triethylsilyl)oxy]-;1-Cyclopentene-1-heptanoic acid, 5-oxo-3-[(triethylsilyl)oxy]-, Methyl ester, (3R)-;1-Cyclopentene-1-heptanoic acid, 5-oxo-3-[(triethylsilyl)oxy]-, Methyl ester, (R)-;(R)-Methyl 7-(5-oxo-3-((triethylsilyl)-oxy)cyclopent-1-en-1-yl)heptanoate
• CAS NO: 118456-54-5
• Molecular Formula: C19H34O4Si
• Molecular Weight: 354.55636
• Product Categories: Chiral Reagents;Intermediates;Miscellaneous Reagents
• Mol File: 118456-54-5.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 413.236oC at 760 mmHg
• Flash Point: 169.262oC
• Appearance: /
• Density: 0.991g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.471
• Storage Temp.: 2-8°C
• Solubility: Dichloromethane
• CAS DataBase Reference: (3R)-5-Oxo-3-[(triethylsilyl)oxy]-1-cyclopentene-1-heptanoic Acid Methyl Ester(CAS DataBase Reference)
• NIST Chemistry Reference: (3R)-5-Oxo-3-[(triethylsilyl)oxy]-1-cyclopentene-1-heptanoic Acid Methyl Ester(118456-54-5)
• EPA Substance Registry System: (3R)-5-Oxo-3-[(triethylsilyl)oxy]-1-cyclopentene-1-heptanoic Acid Methyl Ester(118456-54-5)

Safety Data

• Hazardous Substances Data: 118456-54-5(Hazardous Substances Data)

Usage

Chemical Properties

Colourless Oil

Uses

Intermediate for the synthesis of Misoprostol.

InChI:InChI=1/C19H34O4Si/c1-5-24(6-2,7-3)23-17-14-16(18(20)15-17)12-10-8-9-11-13-19(21)22-4/h14,17H,5-13,15H2,1-4H3/t17-/m0/s1

Upstream product

• 251659-67-3 7-((S)-3-Methanesulfonyloxy-5-oxo-cyclopent-1-enyl)-heptanoic acid methyl ester 
• 42038-75-5 methyl 7-<3(S)-(hydroxy)-5-oxo-1-cyclopenten-1-yl>heptanoate 
• 994-30-9 triethylsilyl chloride 
• 41138-61-8 (4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone 

Downstream Products

• 3434-33-1 prostaglandin E₁ methyl ester 
• 745-65-3 ALPROSTADIL 

Relevant articles and documents

An efficient asymmetric synthesis of prostaglandin E1

An asymmetric total synthesis of Prostaglandin E1 (5) has been achieved in a two-component coupling process. The chiral hydroxycyclopentenone 6 was readily available from furan with 96% ee. The key reaction step was a kinetic enzymatic resolution followed by an in situ inversion. A catalytic asymmetric reduction of the γ-iodo vinyl ketone 19 with the Corey CBS catalyst gave the ω-side chain 7 with >96% ee. Conjugate addition using the reaction with dilithiocyanocuprate followed by mild cleavage of the silyl protective groups and enzymatic hydrolysis of the methyl ester 22 gave (-)-PGE1 5 in high yield.