886841-24-3

Basic information

• Product Name: (1R,4R)-4-[7'-(4-methoxybenzyloxy)heptyl]-2-cyclopenten-1-ol
• Synonyms: (1R,4R)-4-[7'-(4-methoxybenzyloxy)heptyl]-2-cyclopenten-1-ol
• CAS NO: 886841-24-3
• Molecular Weight: 318.456
• Mol File: 886841-24-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (1R,4R)-4-[7'-(4-methoxybenzyloxy)heptyl]-2-cyclopenten-1-ol(CAS DataBase Reference)
• NIST Chemistry Reference: (1R,4R)-4-[7'-(4-methoxybenzyloxy)heptyl]-2-cyclopenten-1-ol(886841-24-3)
• EPA Substance Registry System: (1R,4R)-4-[7'-(4-methoxybenzyloxy)heptyl]-2-cyclopenten-1-ol(886841-24-3)

Safety Data

• Hazardous Substances Data: 886841-24-3(Hazardous Substances Data)

Upstream product

• 60176-77-4 (1S,4R)-4-hydroxy-2-cyclopentenyl acetate 

Downstream Products

• 886841-27-6 (S)-4-[7-(4-Methoxy-benzyloxy)-heptyl]-5-[(E)-oct-2-en-(E)-ylidene]-cyclopent-2-enone 
• 886841-25-4 (R)-4-[7'-(4-methoxybenzyloxy)heptyl]-2-cyclopenten-1-one 

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.