61218-06-2

Basic information

• Product Name: methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate
• Synonyms: methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate
• CAS NO: 61218-06-2
• Molecular Weight: 396.481
• Mol File: 61218-06-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate(61218-06-2)
• EPA Substance Registry System: methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate(61218-06-2)

Safety Data

• Hazardous Substances Data: 61218-06-2(Hazardous Substances Data)

Upstream product

• 80800-65-3 methyl (+)-9α-acetoxy-11α-hydroxy-15-oxoprosta-5(Z),13(E)-dienoate 
• 61408-40-0 methyl 7-(5α-acetoxy-3α-hydroxy-2β-formylcyclopentyl)-5(Z)-heptenoate 
• 110-87-2 dihydropyran 
• 143261-28-3 (Z)-7-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(methoxy-phenylsulfanyl-trimethylsilanyl-methyl)-5-oxo-cyclopentyl]-hept-5-enoic acid methyl ester 
• 143261-31-8 (Z)-7-[(1R,2R,3R,5S)-5-Acetoxy-3-(tert-butyl-dimethyl-silanyloxy)-2-(methoxy-phenylsulfanyl-methyl)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 143261-29-4 (Z)-7-[(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(methoxy-phenylsulfanyl-methyl)-5-oxo-cyclopentyl]-hept-5-enoic acid methyl ester 
• 143261-30-7 (Z)-7-[(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-2-(methoxy-phenylsulfanyl-methyl)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 143261-32-9 (Z)-7-[(1R,2R,3R,5S)-5-Acetoxy-3-hydroxy-2-(methoxy-phenylsulfanyl-methyl)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 61305-35-9 (R)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-enone 
• 64493-06-7 methyl (5Z)-7-iodo-5-heptenoate 
• 110-87-2 3,4-dihydro-2H-pyran 
• 102276-55-1 (Z)-7-[(1R,2S,3R,5S)-5-Acetoxy-2-(1-methoxy-1-methyl-ethoxymethyl)-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 69810-09-9 2-syn-(6-carbomethoxy2-cis-hexenyl)-3-anti-(2,4-dioxa-3,3dimethylpentyl)-4-syn-(tetrahydropyran-2-yloxy)cyclopentan-1-ol 
• 86462-75-1 (E)-5-(tert-butyldimethylsilanyloxy)pent-2-en-1-ol 

Downstream Products

• 62525-17-1 16-(4-chlorophenoxy)-17,18,19,20-tetranor-15-dehydroprostaglandin F_2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether) 
• 62524-96-3 16-(3-chlorophenoxy)-17,18,19,20-tetranor-15-dehydroprostaglandin F_2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether) 
• 745-64-2 PGF_3α 
• 62561-55-1 (Z)-7-[(1R,2R,3R,5S)-5-Acetoxy-2-[(E)-(R)-3-hydroxy-4-(3-trifluoromethyl-phenoxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 62561-51-7 (Z)-7-[(1R,2R,3R,5S)-5-Acetoxy-2-[(E)-(S)-3-hydroxy-4-(3-trifluoromethyl-phenoxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 62525-18-2 (5Z, 13E)-(9α,11α,15R)-9-acetoxy-11-(tetrahydropyran-2-yloxy)-15-hydroxy-16-(4-chlorophenoxy)-17,18,19,20-tetranorprosta-5,13-dienoic acid methyl ester 
• 62525-18-2 (Z)-7-[(1R,2R,3R,5S)-5-Acetoxy-2-[(E)-(S)-4-(4-chloro-phenoxy)-3-hydroxy-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 62561-54-0 16-(4-chlorophenoxy)-17,18,19,20-tetranorprostaglandin F_2α 9-acetate methyl ester 11-(tetrahydropyran-2-yl ether) 
• 62524-97-4 (Z)-7-[(1R,2R,3R,5S)-5-Acetoxy-2-[(E)-(S)-4-(3-chloro-phenoxy)-3-hydroxy-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 62561-48-2 (Z)-7-[(1R,2R,3R,5S)-5-Acetoxy-2-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 62561-52-8 (Z)-7-[(1R,2R,3R,5S)-5-Acetoxy-2-((E)-(S)-3-hydroxy-4-phenoxy-but-1-enyl)-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester 
• 64812-63-1 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-3,4-trans-didehydroprostaglandin F_2α methyl ester 
• 64775-54-8 16-<3-(trifluoromethyl)phenoxy>-17,18,19,20-tetranor-3,4-cis-didehydroprostaglandin F_2α methyl ester 
• 64812-68-6 16-(4-chlorophenoxy)-17,18,19,20-tetranor-3,4-trans-didehydroprostaglandin F_2α methyl ester 

Relevant articles and documents

Total synthesis of prostaglandin F(2α) using nickel-catalyzed stereoselective cyclization of 1,3-diene and tethered aldehyde via transmetalation of nickelacycle with diisobutylaluminum acetylacetonate

Total synthesis of prostaglandin F(2α) utilizing a nickel(0)-catalyzed cyclization of 1,3-diene and tethered aldehyde was achieved. The cyclization proceeded via a transmetalation of nickelacycle with dilsobutylaluminum acetylacetonate ((i)Bu2-ALAC). Thus, the reaction of 19, having a side chain corresponding to the α-chain in PGF(2α) with Ni(cod)2 (10 mol %), PPh3 (20 mol %), and 1,3-cyclohexadiene (25 mol %) in the presence of (i)Bu2-ALAC (1.5 eq) proceeded stereoselectively to give the cyclized product 26 in 54% yield. During the cyclization of 19, the Z-olefin at C-5 in the side chain completely retained its geometry, and the four contiguous chiral carbon centers in PGF(2α) were stereoselectively constructed. Transformation of the key intermediate 19 into PGF(2α) was successfully achieved.

A Divergent Entry into Prostaglandin Synthesis through 1,4-Addition of Methoxy(phenylthio)(trimethylsilyl)methyllithium to 4-Siloxy-2-cyclopentenone

1,4-Addition of methoxy(phenylthio)(trimethylsilyl)methyllithium to 4-siloxy-2-cyclopentenone followed by in situ alkylation of the resulting enolate provides a versatile intermediate for synthesis of prostaglandins.

PROSTAGLANDIN ANALOGUES: Δ15,16-17-Hydroxy-21,22-dihomo(DHPG3.s)

The synthesis of Δ15,16-17-hydroxy-21,22-dihomo PG3.s (DHPG3) is reported.The key step is the condensation of the α,β-unsaturated aldehyde 3 with the phosphonate 12.The configuration of the 17-hydroxyl group was assigned by analogy of the chromatographic behaviour of DHPG3.s with the natural PG.s.