55022-57-6

Basic information

• Product Name: (Z)-7-[(1R,2R,3R,5S)-5-ACETOXY-3-HYDROXY-2-((E)-(S)-3-HYDROXY-OCT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER
• Synonyms: (Z)-7-[(1R,2R,3R,5S)-5-ACETOXY-3-HYDROXY-2-((E)-(S)-3-HYDROXY-OCT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER;(5Z,9α,11α,13E,15S)-9-Acetyloxy-11,15-dihydroxyprosta-5,13-dien-1-oic acid methyl ester
• CAS NO: 55022-57-6
• Molecular Formula: C₂₃H₃₈O₆
• Molecular Weight: 410.54422
• Mol File: 55022-57-6.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (Z)-7-[(1R,2R,3R,5S)-5-ACETOXY-3-HYDROXY-2-((E)-(S)-3-HYDROXY-OCT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-7-[(1R,2R,3R,5S)-5-ACETOXY-3-HYDROXY-2-((E)-(S)-3-HYDROXY-OCT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER(55022-57-6)
• EPA Substance Registry System: (Z)-7-[(1R,2R,3R,5S)-5-ACETOXY-3-HYDROXY-2-((E)-(S)-3-HYDROXY-OCT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER(55022-57-6)

Safety Data

• Hazardous Substances Data: 55022-57-6(Hazardous Substances Data)

Usage

Description

(Z)-7-[(1R,2R,3R,5S)-5-acetoxy-3-hydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid methyl ester is a complex chemical compound characterized by its unique structure, which includes a cyclopentyl ring, a hept-5-enoic acid group, an acetoxy group, and a methyl ester. The presence of hydroxy and enoic acid groups in its structure suggests potential biochemical or pharmaceutical applications, making it an intriguing compound for further research and possible utilization in various fields.

Uses

Used in Pharmaceutical Industry:
(Z)-7-[(1R,2R,3R,5S)-5-acetoxy-3-hydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid methyl ester is used as a potential pharmaceutical compound for its unique combination of functional groups, which may offer novel therapeutic properties and applications in the development of new drugs.
Used in Biochemical Research:
In the field of biochemical research, (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-3-hydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid methyl ester can be utilized as a subject for studying its interactions with various biological systems, potentially leading to a better understanding of its properties and possible applications in medicine.
Used in Chemical Synthesis:
(Z)-7-[(1R,2R,3R,5S)-5-ACETOXY-3-HYDROXY-2-((E)-(S)-3-HYDROXY-OCT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER's complex structure and functional groups make it a candidate for use in chemical synthesis, where it could serve as a building block or intermediate for the creation of other complex molecules with specific applications in various industries.
Used in Material Science:
Given its unique structural features, (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-3-hydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid methyl ester may also find applications in material science, where it could be used to develop new materials with specific properties tailored for various applications.

Upstream product

• 55955-05-0 PGF_2α methyl ester 11,15-bis(tetrahydropyranyl ether) 
• 86462-75-1 (E)-5-(tert-butyldimethylsilanyloxy)pent-2-en-1-ol 
• 377778-93-3 5-((tert-butyldimethylsilyl)oxy)pent-2-en-1-ol 
• 193476-20-9 methyl (5Z,7E)-8-[(1S,2R)-2-(2-tert-butyldimethylsilyloxyethyl)-4,4-dimethyl-3,5-dioxacyclohexyl]-5,7-octadienoate 
• 315716-40-6 methyl (5Z)-7-[(1R,2S,3R,5R)-5-acetoxy-2-(tert-butyldiphenylsilyloxymethyl)-3-(2-oxacyclohexyl)oxy-cyclopentyl]-5-heptenoate 
• 193476-26-5 methyl (5Z)-7-[(1R,2S,3R,5R)-5-acetoxy-2-(tert-butyldiphenylsilyloxymethyl)-3-hydroxycyclopentyl]-5-heptenoate 
• 56575-39-4 methyl (5Z)-7-{(1R,2R,3R,5R)-5-acetoxy-3-(2-oxacyclohexyl)oxy-[(1E)-3-oxo-1-octenyl]cyclopentyl}-5-heptenoate 
• 193476-24-3 methyl (5Z)-7-{(1R,6S,7R,8R)-8-acetoxy-3,3-dimethyl-2,4-dioxabicyclo[3.3.0]-nonan-7-yl}-5-heptenoate 
• 193476-15-2 methyl (2E)-2-[(1S,2R)-tert-butyldimethylsilyloxyethyl-4,4-dimethyl-3,5-dioxacyclohexyl]2-propenoate 
• 315716-30-4 methyl (5Z,7E)-8-[(1S,2R)-4,4-dimethyl-3,5-dioxa-2-(2-hydroxyethyl)cyclohexyl]-5,7-octadienoate 
• 193476-23-2 methyl (5Z)-8-{(1R,6S,7R,8S)-3,3-dimethyl-2,4-dioxa-8-hydroxbicyclo[4.3.0]-nonan-7-yl}-5-heptenoate 
• 193476-21-0 methyl (5Z,7E)-8-[(1S,2R)-4,4-dimethyl-3,5-dioxa-2-(2-oxoethyl)cyclohexyl]-5,7-octadienoate 
• 315716-36-0 (1R,6S,7R,8S)-8-tert-butyldimethylsilyloxy-3,3-dimethyl-2,4-dioxa-7-(2-propenyl)-bicyclo[4.3.0]nonan-8-ol 
• 193476-16-3 (2E)-3-[(1S,2R)-2-(2-tert-butyldimethylsilyloxyethyl)-4,4-dimethyl-3,5-dioxacyclohexyl]-2-propen-1-ol 

Downstream Products

• 33854-16-9 (+)-prostaglandin F_2α 
• 551-11-1 dinoprost 
• 13228-05-2 15-epi-PGF_2α 

Relevant articles and documents

Synthesis of (5E)- and (5Z)-11-Deoxy-6,11α-epoxy-Δ5-prostaglandin F1α Sodium Salts: 6,11α-Enol Ether Isomers of Prostacyclin

The key intermediates, (5S,6R)- and (5R,6R)-11-deoxy-6,11α-epoxy-5-hydroxy cyclic ethers, 22a,b, were prepared from the reaction of a C-9 silyl PGF2α derivative 12 with mercuric acetate (oxymercuration), followed by conversion of the mercurioacetate substituent to a hydroxy group.Attempts to construct the 6,11α oxygen bridge by reaction of 12 and other C-9 protected PGF2α derivatives with iodine, N-bromosuccinimide, and phenylselenenyl chloride were unsuccessful.Reaction of 11 and 12 with iodine resulted in removal of the C-9 blocking group and the isolation of 6,9-iodo cyclic ether products.Treatment of 13 with phenylselenenyl chloride gave the β-chlorophenylselenenyl addition adduct 18.Conversion of alcohols 22a,b to their mesylate derivatives, 25a,b, and subsequent reaction with potassium methoxide in dimethyl sulfoxide afforded the labile Δ5 enol ethers, 29a,b.The success of this elimination reaction was critically dependent on the base, the reaction solvent, and the workup conditions.The structural assignments of 29a,b were based on their spectral properties and hydrolysis to 6-keto-PGF1α methyl ester.The stereoconfiguration at C-6 was assigned by conversion of the oxymercuration product obtained from 12 to the 5,6-dihydro-6,11α-cyclic ether 20.The C-5 stereoconfiguration of alcohols 22a,b was established by the mode of formation of enol ethers 29a,b.In contrast to PGI2 methyl ester, 29a,b in aqueous acid showed a greater tendency to form the internal ketal 34 during hydrolysis to 6-keto-PGF1α methyl ester.

Total Synthesis of Prostaglandin F2α via Nickel-Promoted Stereoselective Cyclization of 1,3-Diene and Aldehyde

The total synthesis of prostaglandin F2α (PGF2α) was accomplished via nickel-promoted cyclization of 1,3-diene and aldehyde in a chain in the presence of 1,3-cyclohexadiene (1,3-CHD). The cyclization of 16 prepared in an optically active form from chiral epoxy alcohol 10 stereoselectively gave the key intermediate 18, which has both an α-chain and the four contiguous chiral carbon centers in PGF2α, in a one-pot reaction. Intermediate 18 was successfully transformed into PGF2α.