79172-00-2

Upstream product

• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 62961-72-2 Corey aldehyde 
• 122517-79-7 7α-trimethylsilyloxy-6β-formyl-2-oxabicyclo<3.3.0>octan-3-one 
• 118457-23-1 7α-hydroxy-6β-hydroxymethylene-2-oxabicyclo<3.3.0>octan-3-one bistrimethylsilyl ether 
• 51638-93-8 7α-hydroxy-6β-(3'-hydroxy-4'-phenoxy-1'E-butenyl)-2-oxabicyclo<3.3.0>octan-3-one 
• 871669-32-8 7α-hydroxy-6β-(3'-oxo-4'-phenoxy-1'E-butenyl)-2-oxabicyclo<3.3.0>octan-3-one 
• 871669-30-6 7α-trimethylsilyloxy-6β-(3'-oxo-4'-phenoxy-1'E-butenyl)-2-oxabicyclo<3.3.0>octan-3-one 
• 127702-12-9 7α-trimethylsilyloxy-6β-(3'α-trimethylsilyloxy-4'-phenoxy-1'E-butenyl)-2-oxabicyclo<3.3.0>octan-3-one 
• 52533-65-0 [4-(methanesulfonylaminocarbonyl)-n-butyl]triphenylphosphonium bromide 
• 79171-98-5 Biphenyl-4-carboxylic acid (3aR,4R,5R,6aS)-4-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 286840-19-5 (3aR,4R,5R,6aS)-4-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol 
• 51638-93-8 (3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-hexahydro-cyclopenta[b]furan-2-one 
• 2065-23-8 methyl 2-phenoxyacetate 
• 40665-68-7 dimethyl (3-phenoxy-2-oxopropyl)phosphonate 

Downstream Products

• 127718-29-0 N-{(Z)-7-[(1R,2R,3R,5S)-5-Hydroxy-2-((E)-(R)-4-phenoxy-3-trimethylsilanyloxy-but-1-enyl)-3-trimethylsilanyloxy-cyclopentyl]-hept-5-enoyl}-methanesulfonamide 
• 60325-46-4 Sulprostone 

Relevant academic research and scientific papers

PROSTANOIDS. XXIX. SELECTIVE OXIDATION OF 7α-HYDROXY-6β-HYDROXYMETHYLENE-2-OXABICYCLOOCTAN-3-ONE BISTRIMETHYLSILYL ETHER BY REAGENTS BASED ON CHROMIUM(VI) AS KEY STAGE IN SYNTHESIS OF SULPROSTONE

7α-Hydroxy-6β-(3-oxo-4-phenoxy-1E-butenyl)-2-oxabicyclooctan-3-one was synthesized by the selective oxidation of 7α-hydroxy-6β-hydroxymethylene-2-oxabicyclooctan-3-one bistrimethylsilyl ether with CrO3*2Py/SiO2 and subsequent condensation of the intermediate 7α-trimethylsiloxy-6β-formyl-2-oxabicyclooctan-3-one with dimethyl 2-oxo-3-phenoxypropylphosphonate.The product was then converted into the methanesulfonamide of 16-phenoxy-17,18,19,20-tetranorprostaglandin E2 (sulprostone).

N-(Methanesulfonyl)-16-phenoxyprostaglandincarboxamides: Tissue-Selective, Uterine Stimulants

In an effort to develop tissue-selective prostaglandin analogues resistant to the metabolic inactivating pathways of the natural materials, hybrid compounds modified both at C-1 with a sulfonimide moiety and in the n-amylcarbinol side chain with substituted phenoxy groups were synthesized and evaluated in a variety of in vitro and in vivo models.Several of these analogues exhibited potent, tissue-selective, uterine stimulant activity, a finding subsequently confirmed in clinical studies with one member of this series, N-(methanesulfonyl)-16-phenoxy-ω-tetranor-PGE2-carboxamide (CP-34089/ZK-57671, sulprostone).