42038-75-5

Basic information

• Product Name: METHYL (S)-(-)-3-HYDROXY-5-OXO-1-CYCLOPENTENE-1-HEPTANOATE
• Synonyms: methyl (S)-(-)-3-hydroxy-5-oxo-1-cyclo-pentene-1-;METHYL (S)-(-)-3-HYDROXY-5-OXO-1-CYCLO-P ENTENE-1-HEPTANOATE,97% EE/HPLC;Methyl (S)-(-)-3-hydroxy-5-oxo-cyclopentene-1-heptanoate;METHYL (S)-(-)-3-HYDROXY-5-OXO-1-CYCLOPENTENE-1-HEPTANOATE;(S)-Methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)heptanoate
• CAS NO: 42038-75-5
• Molecular Formula: C13H20O4
• Molecular Weight: 240.3
• Product Categories: Chiral Building Blocks;Esters;Organic Building Blocks
• Mol File: 42038-75-5.mol
• Article Data: 4

Chemical Properties

• Melting Point: 59-62 °C(lit.)
• Boiling Point: 378.435°C at 760 mmHg
• Flash Point: 138.885°C
• Appearance: /
• Density: 1.125g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.504
• PKA: 12.95±0.40(Predicted)
• CAS DataBase Reference: METHYL (S)-(-)-3-HYDROXY-5-OXO-1-CYCLOPENTENE-1-HEPTANOATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (S)-(-)-3-HYDROXY-5-OXO-1-CYCLOPENTENE-1-HEPTANOATE(42038-75-5)
• EPA Substance Registry System: METHYL (S)-(-)-3-HYDROXY-5-OXO-1-CYCLOPENTENE-1-HEPTANOATE(42038-75-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 42038-75-5(Hazardous Substances Data)

Usage

Uses

Norprostol, (-)- is an intermediate in synthesis of prostaglandins,used for the treatment of gastric and duodenal ulcers.

InChI:InChI=1/C13H20O4/c1-17-13(16)7-5-3-2-4-6-10-8-11(14)9-12(10)15/h8,11,14H,2-7,9H2,1H3/t11-/m1/s1

Upstream product

• 108-05-4 vinyl acetate 
• 40098-26-8 methyl 7-(3-hydroxy-5-oxocyclopent-1-en-1-yl)heptanoate 

Downstream Products

• 118456-54-5 methyl-7-[5-oxo-3(R)-[(triethylsilyl)oxy]-1-cyclopenten-1yl]-heptanoate 
• 3434-33-1 prostaglandin E₁ methyl ester 
• 41138-61-8 (4R)-4-hydroxy-2-(6-methoxycarbonylhexyl)cyclopent-2-enone 
• 745-65-3 ALPROSTADIL 
• 308103-47-1 7-[3-(tert-butyl-dimethyl-silanyloxy)-5-oxo-cyclopent-1-enyl]-heptanoic acid methyl ester 

Relevant articles and documents

An efficient synthesis of enantiomerically pure (1R,2S,5S)- and (1S,2R,5R)-rosaprostol methyl esters

We report a concise synthesis of the enantiomerically pure 1,2-trans-1,5-cis-methyl esters of rosaprostol, a prostaglandin derivative used for the treatment of gastric and duodenal ulcers, using as key step the chemo- and stereoselective Michael addition of a Grignard reagent to an unprotected hydroxycyclopentenone. Georg Thieme Verlag Stuttgart.

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.