676236-13-8

Basic information

• Product Name: (4S,5S)-5-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-octyl]-4-[7-(4-methoxy-benzyloxy)-hept-2-ynyl]-cyclopent-2-enone
• CAS NO: 676236-13-8
• Molecular Weight: 570.885
• Mol File: 676236-13-8.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: (4S,5S)-5-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-octyl]-4-[7-(4-methoxy-benzyloxy)-hept-2-ynyl]-cyclopent-2-enone(CAS DataBase Reference)
• NIST Chemistry Reference: (4S,5S)-5-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-octyl]-4-[7-(4-methoxy-benzyloxy)-hept-2-ynyl]-cyclopent-2-enone(676236-13-8)
• EPA Substance Registry System: (4S,5S)-5-[(S)-3-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-octyl]-4-[7-(4-methoxy-benzyloxy)-hept-2-ynyl]-cyclopent-2-enone(676236-13-8)

Safety Data

• Hazardous Substances Data: 676236-13-8(Hazardous Substances Data)

Upstream product

• 193292-90-9 (S)-1,3-octanediol 
• 676235-98-6 [(1S,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-cyclopenten-1-yl]ethanal 
• 676236-10-5 ether compound 
• 676236-07-0 (S)-1,3-[(tert-butyldimethylsilyl)oxy]octane 
• 676236-11-6 (1S,4R)-4-[7'-(4-methoxybenzyloxy)-2'-heptynyl]-2-cyclopenten-1-ol 
• 869801-11-6 (1S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-[3',3'-dibromo-2'-propenyl]-2-cyclopentene 
• 676236-08-1 (3S)-3-{[1-(tert-butyl)-1,1-dimethylsilyl]oxy}octan-1-ol 
• 676236-09-2 (1S,4R)-1-[(tert-butyldimethylsilyl)oxy]-4-(2'-propynyl)-2-cyclopentene 
• 426226-00-8 dimethyl 2-((1R,4S)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-en-1-yl)malonate 
• 660430-04-6 methyl 2-((1S,4S)-4-((tert-butyldimethylsilyl)oxy)cyclopent-2-en-1-yl)acetate 
• 115074-49-2 (1R,4S)-4-[(tert-butyldimethylsilyl)oxy]-2-cyclopentene-1-yl acetate 
• 120052-54-2 (1S,3S)-1-hydroxy-3-(methyl-carboxymethyl)-4-cyclopentene 
• 120052-50-8 2-<(1R,4S)-4-hydroxycyclopent-2-enyl>malonsaeure-dimethylester 
• 60410-16-4 (1R,4S)-4-hydroxy-2-cyclopentene-1-yl acetate 

Downstream Products

• 676236-14-9 dienone compound 

Relevant articles and documents

Highly efficient total synthesis of Δ12-PGJ2, 15-deoxy-Δ12,14-PGJ2, and their analogues

Palladium-catalyzed reaction of TBS ether of 4-cyclopentene-1,3-diol monoacetate (>95% ee) with an anion derived from methyl malonate and a base such as t-BuOK and LDA proceeded highly efficiently and reproducibly. The product obtained in >90% isolated yield was transformed in five steps into the key cyclopentenone possessing the α-chain at the γ position. Aldol reaction of this enone with the ω-chain aldehyde afforded the aldol adduct, and exposure of the derived mesylate to Al2O3 furnished the cross-conjugated dienone of the full structure. Finally, functional group manipulation furnished Δ12-PGJ2 efficiently. Similarly, 15-deoxy-Δ12,14-PGJ2, 5,6-acetylene analogues, and a 5,6-dihydro analogue were synthesized.