112329-45-0

Basic information

• Product Name: 11,15-O-bis(tert-butyldimethylsilyl)PGI₂ methyl ester
• Synonyms: 11,15-O-bis(tert-butyldimethylsilyl)PGI₂ methyl ester
• CAS NO: 112329-45-0
• Molecular Weight: 595.023
• Mol File: 112329-45-0.mol

Chemical Properties

• CAS DataBase Reference: 11,15-O-bis(tert-butyldimethylsilyl)PGI₂ methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 11,15-O-bis(tert-butyldimethylsilyl)PGI₂ methyl ester(112329-45-0)
• EPA Substance Registry System: 11,15-O-bis(tert-butyldimethylsilyl)PGI₂ methyl ester(112329-45-0)

Safety Data

• Hazardous Substances Data: 112329-45-0(Hazardous Substances Data)

Upstream product

• 79672-82-5 methyl 7-((1R,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-2-((S,E)-3-(tert-butyldimethylsilyloxy)oct-1-enyl)-5-hydroxycyclopentyl)-6-oxoheptanoate 
• 59926-53-3 5,6-didehydro-11,15-O-bis(tert-butyldimethylsilyl)PGF_2α methyl ester 

Relevant articles and documents

The Three-Component Coupling Synthesis of Prostaglandins

A convergent one-pot construction of the prostaglandin (PG) framework has been accomplished by the organocopper-mediated conjugate addition of the S configurated ω side-chain unit to a protected (R)-4-hydroxy-2-cyclopentenone followed by trapping of the enolate intermediate by α side-chain alkyl halides.Transmetalation with use of triphenyltin chloride at the enolate stage serves as key operation for the succesful three-component coupling synthesis.The use of methyl (Z)-7-iodo-5-heptenoate as the α side-chain component allows short synthesis of PGE2 and PGD2.Introduction of a triple bond at the C-5-C-6 positions with methyl 7-iodo-5-heptynoate as the α side-chain synthon has opened a general entry of PGs.The protected 5,6-didehydro-PGE2 derivatives are convertible to a variety of PGs of 1 and 2 series by the controlled hydrogenation of the C-5-C-6 unsaturated bonds and α-selective (100percent) reduction of the C-9 keto function, if necessary.Lithium aluminum hydride reagents modified by (R)- and (S)-2,2'-dihydroxy-1,1'-binaphthyl exhibit a unique kinetic discrimination in reduction of PGE type compounds.A protected 5,6-didehydro-PGF2α has been transformed stereoselectively to PGI2 by using intramolecular alkoxypalladation/depalladation as the key step.

Nitro-Olefin Trapping Reactions of Enolates In Situ Generated by Conjugate Addition Reaction: Short Syntheses of PGE1, 6-Oxo-PGE1, 6-Oxo-PGF1α, and PGI2

The nitro-olefin trapping of the enolates in situ generated by conjugate addition of organocopper reagents to the chiral oxygenated cyclopentenone synthon, R-4, gives the three-component coupling products in a regiospecific manner.The intermediary nitronate anion 17 is further transformed into the nitro compound or 6-oxo-PGE1 (19) in a single pot.This coupling reaction is applicable to syntheses of naturally occurring prostaglandins such as PGE1, 6-oxo-PGF1α, and PGI2.