114868-74-5

Basic information

• Product Name: (2E)-7-{(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methylnon-1-en-1-yl]-5-oxocyclopentyl}hept-2-enoic acid (non-preferred name)
• Synonyms: 2E,11a,13E,15S,17S)-11,15-Dihydroxy-17,20-dimethyl-9-oxoprosta-2,13-dien-1-oic Acid; (E)-7-((1R,2R,3R)-3-Hydroxy-2-((E)-(3S,5S)-3-hydroxy-5-methyl-1-nonenyl)-5-oxocyclopentyl)-2-heptenoic acid; 17S-Methyl-w-homo-trans-D2-PGE1; Limaprost; ONO 1206; (2E)-7-[(1R,2R,3R)-3-Hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonen-1-yl]-5-oxocyclopentyl]-2-heptenoic acid; 2-Heptenoicacid, 7-[(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonenyl]-5-oxocyclopentyl]-,(2E)-; Prosta-2,13-dien-1-oic acid,11,15-dihydroxy-17,20-dimethyl-9-oxo-, (2E,11a,13E,15S,17S)-; 17S,20-Dimethyl-trans-D2-PGE1; OP1206; (2E)-7-{(1R,2R,3R)-3-Hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonen-1-yl]-5-oxocyclopentyl}-2-heptenoic acid (non-preferred name); (E)-7-((1R,2R,3R)-3-Hydroxy-2-((E)-(3S,5S)-3-hydroxy-5-methyl-1-nonenyl)-5-oxocyclopentyl)-2-heptenoic acid 17S-Methyl-w-homo-trans-D2-PGE1; 9-Oxo-11a,15a-dihydroxy-17S,20-dimethylprosta-trans-2,trans-13-dienoic Acid
• CAS NO: 114868-74-5
• Molecular Formula: C₂₂H₃₆O₅
• Molecular Weight: 380.5182
• Mol File: 114868-74-5.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 550.6°C at 760 mmHg
• Flash Point: 300.9°C
• Density: 1.118g/cm³
• Vapor Pressure: 2.03E-14mmHg at 25°C
• Refractive Index: 1.55
• CAS DataBase Reference: (2E)-7-{(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methylnon-1-en-1-yl]-5-oxocyclopentyl}hept-2-enoic acid (non-preferred name)(CAS DataBase Reference)
• NIST Chemistry Reference: (2E)-7-{(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methylnon-1-en-1-yl]-5-oxocyclopentyl}hept-2-enoic acid (non-preferred name)(114868-74-5)
• EPA Substance Registry System: (2E)-7-{(1R,2R,3R)-3-hydroxy-2-[(1E,3S,5S)-3-hydroxy-5-methylnon-1-en-1-yl]-5-oxocyclopentyl}hept-2-enoic acid (non-preferred name)(114868-74-5)

Safety Data

• Hazardous Substances Data: 114868-74-5(Hazardous Substances Data)

Upstream product

• 149585-88-6 C₂₉H₅₆O₄Si₂ 
• 91971-41-4 5-(2-Furoyl)pentansaeure-methylester 
• 627-91-8 adipic acid monomethyl ester 

Downstream Products

• 853998-94-4 (2E)-7-{(1R,2S)-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonenyl]-5-oxo-3-cyclopenten-1-yl}-2-heptenoic acid 
• 75554-85-7 C₂₂H₃₆O₅ 

Relevant articles and documents

Synthesis of Allyl Ester of Prostaglandin E and the Conversion of the Allyl Ester Moiety into Carboxylic Acid by Chemical Method. A Highly Practical Synthesis of Natural PGE1 and Limaprost

Synthesis of prostaglandin E allyl ester via two-component coupling process and the conversion of the allyl ester moiety into free carboxylic acid by the reaction with HCO2H-Et3N in the presence of a palladium catalyst has been described.

Key intermediate for preparing limaprost and application thereof

The invention provides a key intermediate, i.e., a compound as shown in a formula A which is described in the specification, for synthesis of limaprost. In the formula, R1 is selected from a group consisting of a tert-butyldimethylsilyl group, a tert-butyldiphenylsilyl group, a triethylsilyl group, a trimethylsilyl group and a tetrahydropyranyl group; R2 is selected from a group consisting of a tert-butyldimethylsilyl group, a tert-butyldiphenylsilyl group, a triethylsilyl group, a trimethylsilyl group and a tetrahydropyranyl group; R3 is selected from a benzyl group or a substituted benzyl group; and R4 is selected from a group consisting of H, an acetyl group, a chloroacetyl group, a methoxyacetyl group, a benzoyl group or a substituted benzoyl group. The invention also provides a route for synthesizing limaprost from the compound. The route has the advantages of good chiral control of preparation process, capacity of constructing a double-bond structure through multiple Wittig reactions, high efficiency, low production cost, etc.

Key intermediate for preparing Limaprost and use thereof

The invention provides a key intermediate compound shown in the formula IV for Limaprost synthesis and a route for synthesis of Limaprost from the compound. The route has the advantages of less synthesis processes, high synthesis efficiency and low production cost.