193476-26-5

Basic information

• Product Name: 5-Heptenoic acid, 7-[(1R,2S,3R,5S)-5-(acetyloxy)-2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy] methyl]-3-hydroxycyclopentyl]-, methyl ester, (5Z)-
• CAS NO: 193476-26-5
• Molecular Formula: C32H44O6Si
• Molecular Weight: 552.783
• Mol File: 193476-26-5.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 5-Heptenoic acid, 7-[(1R,2S,3R,5S)-5-(acetyloxy)-2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy] methyl]-3-hydroxycyclopentyl]-, methyl ester, (5Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 5-Heptenoic acid, 7-[(1R,2S,3R,5S)-5-(acetyloxy)-2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy] methyl]-3-hydroxycyclopentyl]-, methyl ester, (5Z)-(193476-26-5)
• EPA Substance Registry System: 5-Heptenoic acid, 7-[(1R,2S,3R,5S)-5-(acetyloxy)-2-[[[(1,1-dimethylethyl)diphenylsilyl]oxy] methyl]-3-hydroxycyclopentyl]-, methyl ester, (5Z)-(193476-26-5)

Safety Data

• Hazardous Substances Data: 193476-26-5(Hazardous Substances Data)

Upstream product

• 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 
• 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 
• 193476-17-4 (4R,5S)-4-{5-[(1E)-1,3-butadienyl]}-4-(2-tert-butyldimethylsilyloxyethyl)-2,2-dimethyl-1,3-dioxa-cyclohexane 
• 193476-14-1 (4R,5S)-4-(2-tert-butyldimethylsilyloxyethyl)-2,2-dimethyl-1,3-dioxa-5-ethenylcyclohexane 
• 315716-32-6 2-{(1R,6S)-6-[(1E)-1,3-butadienyl]-3,3-dimethyl-2,4-dioxacyclohexyl}ethanol 
• 193476-19-6 (1R,6S,7R,8S)-3,3-dimethyl-2,4-dioxa-7-(2-propenyl)bicyclo[4.3.0]nonan-8-ol 

Downstream Products

• 551-11-1 dinoprost 
• 55022-57-6 methyl (5Z)-7-{(1R,2R,3R,5R)-5-acetoxy-3-hydroxy-2-[(1E,3S)-3-hydroxy-1-octenyl]cyclopentyl}-5-heptenoate 
• 61218-06-2 methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate 
• 61218-10-8 methyl (5Z)-7-{(1R,2S,3R,5R)-5-acetoxy-2-hydroxymethyl-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate 
• 33854-16-9 (+)-prostaglandin F_2α 
• 315716-40-6 methyl (5Z)-7-[(1R,2S,3R,5R)-5-acetoxy-2-(tert-butyldiphenylsilyloxymethyl)-3-(2-oxacyclohexyl)oxy-cyclopentyl]-5-heptenoate 

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.