23453-26-1

Basic information

• Product Name: (+/-)-prostaglandin E₂ methyl ester
• CAS NO: 23453-26-1
• Molecular Weight: 366.498
• Mol File: 23453-26-1.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: (+/-)-prostaglandin E₂ methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (+/-)-prostaglandin E₂ methyl ester(23453-26-1)
• EPA Substance Registry System: (+/-)-prostaglandin E₂ methyl ester(23453-26-1)

Safety Data

• Hazardous Substances Data: 23453-26-1(Hazardous Substances Data)

Upstream product

• 31660-11-4 7-[(2S,3S)-3-Hydroxy-2-((E)-(R)-3-hydroxy-oct-1-enyl)-5-oxo-cyclopentyl]-hept-5-ynoic acid methyl ester 
• 103904-98-9 methyl (5Z)-7-<6-<(1E)-3-<(tert-butyldimethylsilyl)oxy>-1-octenyl>-2,2-dimethyl-4-oxo-3aβ,5β,6α,6aβ-tetrahydro-4H-cyclopenta-1,3-dioxol-5-yl>-5-heptenoate 
• 103904-95-6 meso-4β,6-diacetoxy-2,2-dimethyl-3αβ,5,6α,6αβ-tetrahydro-4H-cyclopenta-1,3-dioxole 
• 115420-61-6 3α,5α-diacetoxy-1β,2β-cyclopentanediol 
• 103905-00-6 6-<(1'E)-3'-<(tert-butyldimethylsilyl)oxy>-1'-octenyl>-2,2-dimethyl-3aβ,5,6α,6aβ-tetrahydro-4H-cyclopenta-1,3-dioxol-4-one 
• 542-92-7 cyclopenta-1,3-diene 
• 64244-45-7 methyl (Z)-7-hydroxy-5-heptenoate 
• 40269-54-3 (+/-)-2,2-dimethyl-3αβ,6αβ-dihydro-4H-cyclopenta-1,3-dioxol-4-one 
• 60134-93-2 3-(tert-butyldimethylsilyloxy)oct-1-yne 
• 64493-06-7 methyl (5Z)-7-iodo-5-heptenoate 
• 50781-91-4 methyl 7-hydroxy-5-heptynoate 
• 29783-26-4 cis-4-cyclopentene-1,3-diol 
• 54664-61-8 cis-1,4-diacetoxy-2-cyclopentene 
• 51751-83-8 methyl (5Z)-7-bromo-5-heptenoate 

Downstream Products

• 31753-19-2 (Z)-7-[(1S,2R)-2-((E)-(R)-3-Hydroxy-oct-1-enyl)-5-oxo-cyclopent-3-enyl]-hept-5-enoic acid methyl ester 

Relevant articles and documents

Enantioselective Rh-Mediated Synthesis of (-)-PGE2 Methyl Ester

Intramolecular Rh(II) carboxylate catalyzed cyclization of an α-diazo β-methylene ketone to form a fused cyclopropane is shown to compete efficiently with β-hydride elimination, so long as a catalyst derived from an electron-donating carboxylate is used.C

PALLADIUM(0) CATALYZED REACTIONS OF 1,4-EPIPEROXIDES

The Pd(PPh3)4 catalyzed reaction of 2,3-saturated and 2,3-unsaturated 1,4-epiperoxides proceeds by courses markedly different from those of the previously reported transition metal catalyses.The Pd(0)-promoted reaction of 2,3-saturated epiperoxides gives the corresponding 4-hydroxy ketones and 1,4-diols as the major products.From 2,3-dedihydroepiperoxides are formed the corresponding 4-hydroxy enones, syn-1,2;3,4-diepoxides, and 1,4-diols.The results are interpreted in terms of competing Pd(0)/Pd(II) exchange mechanisms.Exposure of prostaglandin (PG) H2 methyl esterto Pd(PPh3)4 produces a mixture of methyl esters of PGD2, PGE2, PGF2α, and (5Z,8E,10E,12S)-12-hydroxy-5,8,10-heptadecatrienoic acid.

Total Synthesis of (+/-)-Prostaglandin E2 Methyl Ester from exo-2-Bromo-endo-3-hydroxybicycloheptan-6-one using Dimethyl-t-butylsilyl Protected Intermediates

Peracetic acid oxidation at -78 deg C of the dihydroxybicyclohepten-6-one (23) afforded the dihydroxylactone (24) which was protected as its bisdimethyl-t-butylsilyl ether (26) and reduced to the corresponding lactol (27).A Wittig reaction on (27), carried out in benzene with a short reaction time, gave mainly the required 11α-silyl ether (28) together with a trace of the 9α-silyl ether (29) which results from 1,5-migration of the silyl group.Oxidation of (28) followed by quantitative deprotection using aqueous HF in acetonitrile afforded (+/-)-PGE2 methyl ester (20).This short stereo- and regioselective total synthesis proceeds in an overall yield of 10percent starting from cyclopentadiene.