81834-79-9

Basic information

• Product Name: 7-(3-hydroxy-5-oxo-1-cyclopenten-1-yl)-(5Z)--Heptenoic acid-1-Methylethyl ester
• Synonyms: 7-(3-hydroxy-5-oxo-1-cyclopenten-1-yl)-(5Z)--Heptenoic acid-1-Methylethyl ester;(5Z)-7-(3-Hydroxy-5-oxo-1-cyclopenten-1-yl)-5-heptenoic acid 1-methylethyl ester
• CAS NO: 81834-79-9
• Molecular Formula: C15H22O4
• Molecular Weight: 266.33278
• Mol File: 81834-79-9.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7-(3-hydroxy-5-oxo-1-cyclopenten-1-yl)-(5Z)--Heptenoic acid-1-Methylethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 7-(3-hydroxy-5-oxo-1-cyclopenten-1-yl)-(5Z)--Heptenoic acid-1-Methylethyl ester(81834-79-9)
• EPA Substance Registry System: 7-(3-hydroxy-5-oxo-1-cyclopenten-1-yl)-(5Z)--Heptenoic acid-1-Methylethyl ester(81834-79-9)

Safety Data

• Hazardous Substances Data: 81834-79-9(Hazardous Substances Data)

Upstream product

• 1190883-10-3 (Z)-8-(furan-2-yl)-8-hydroxyoct-5-enoate 
• 98-01-1 furfural 
• 1012036-78-0 4-(tert-butyldimethylsilyloxy)-4-(furan-2-yl)-butene 
• 2067-33-6 5-bromopentanoic acid 
• 17814-85-6 (4-carboxybutyl)triphenylphosphonium bromide 
• 1190883-06-7 4-(tert-butyldimethylsilyloxy)-4-(furan-2-yl)-butane-1,2-diol 
• 1190883-07-8 3-(tert-butyldimethylsilyloxy)-3-(furan-2-yl)propanal 
• 1190883-11-4 (Z)-8-(furan-2-yl)-8-hydroxy-oct-5-enoic acid 
• 1190883-08-9 isopropyl (Z)-8-(tert-butyldimethylsilyloxy)-8-(furan-2-yl)-oct-5-enoate 
• 1190883-23-8 (Z)-8-(tert-butyldimethylsilyloxy)-8-(furan-2-yl)-oct-5-enoic acid 
• 1415237-38-5 (4-methoxyphenyl)methanaminium (Z)-8-(furan-2-yl)-8-hydroxy-oct-5-enoate 

Relevant articles and documents

The manufacture of a homochiral 4-silyloxycyclopentenone intermediate for the synthesis of prostaglandin analogues

A process is described for the synthesis of kilogram quantities of homochiral 4-silyloxycyclopentenone (R)-1, a key intermediate useful for the synthesis of a plurality of prostaglandin analogue drugs. Cyclopentenone (R)-1 was synthesized in 14 isolated steps from furfural. Key steps in the synthesis include a Wittig reaction, Piancatelli rearrangement, and an enzymatic resolution featuring in situ recycling of the undesired enantiomer furnishing the desired homochiral alcohol in ≥99.5% ee. As a retort to the unsatisfactory coformation of about 8% at best of the trans-olefin in the Wittig reaction, a change to the order of several steps and the identification of a recrystallisable, amine salt derivative, 2, allowed the unwanted isomer to be controlled to as low as 0.2%.