53906-54-0

Usage

Uses

Used in Veterinary Medicine:
CLOPROSTENOL LACTONE DIOL is used as a luteolytic agent for inducing estrus and regulating reproductive cycles in cattle and horses. It functions by causing the corpus luteum to regress, which leads to the release of prostaglandin F2-alpha, thereby inducing luteolysis and initiating the onset of estrus.
Used in Research and Development:
CLOPROSTENOL LACTONE DIOL is used as a potential therapeutic agent in the study of its anti-inflammatory properties and its potential application in the treatment of cystic fibrosis and other respiratory conditions. This involves ongoing research to explore its efficacy and safety in these areas.

InChI:InChI=1/C17H19ClO5/c18-10-2-1-3-12(6-10)22-9-11(19)4-5-13-14-7-17(21)23-16(14)8-15(13)20/h1-6,11,13-16,19-20H,7-9H2/b5-4+/t11-,13-,14-,15-,16+/m1/s1

Upstream product

• 53872-62-1 Cloprostenol 
• 26054-46-6 (-)-(1S,5R)-2-oxabicyclo[3.3.0]oct-6-en-3-one 
• 130325-32-5 Formic acid (3aR,4S,5R,6aS)-4-formyloxymethyl-2-oxo-hexahydro-cyclopenta[b]furan-5-yl ester 
• 62961-72-2 Corey aldehyde 
• 32233-40-2 (3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one 
• 31752-99-5 (-)-Corey lactone 5-(4-phenylbenzoate) 
• 52094-98-1 ethyl (3-chlorophenoxy)acetate 
• 108-43-0 3-monochlorophenol 
• 38754-71-1 (3aR,4R,5R,6aS)-4-formyl-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl biphenyl-4-carboxylate 
• 54324-79-7 (3aR,4R,5R,6aS)-4-((E)-4-(3-chlorophenoxy)-3-oxobut-1-enyl)-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1′-biphenyl]-4-carboxylate 
• 40665-94-9 dimethyl 3-(3-chlorophenoxy)-2-oxopropylphosphonate 
• 53872-62-1 [3aα,4α(E),5β,6aα]-(+/-)-4-[4-(3-chlorophenoxy)-3-oxo-1-butenyl]-hexahydro-5-hydroxy-2H-cyclopenta[b]-furan-2-one 

Downstream Products

• 121221-68-9 (1SR, 5RS, 6RS, 7RS)-7-tert-butyldimethylsilyloxy-6-<(3RS)-3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1(E)-en-1-yl>-2-oxabicyclo<3.3.0>octan-3-one 
• 109323-19-5 (1SR,5RS,6RS,7RS)-6-<(3SR)-4-(3-chlorophenoxy)-3-(1-ethoxy-ethoxy)-1(E)-butenyl>-7-(1-ethoxy-ethoxy)-2-oxabicyclo<3.3.0>octan-3-one 
• 54276-21-0 (+)-cloprostenol 
• 109323-20-8 (3aR,4R,5R,6aS)-4-((3R,E)-4-(3-chlorophenoxy)-3-(1-ethoxyethoxy)but-1-enyl)-5-(1-ethoxyethoxy)hexahydro-2Hcyclopenta[b]furan-2-ol 
• 56687-85-5 methyl (8R,9S,11R,12S,15S)-16-(m-chlorophenoxy)-9,11,15-trihydroxy-17,18,19,20-tetranor-5Z,13E-prostadienoate 
• 206555-98-8 cloprostenol 
• 89560-44-1 (3aR,4R,5R,6aS)-4-[(E)-4-(3-Chloro-phenoxy)-3-hydroxy-but-1-enyl]-hexahydro-cyclopenta[b]furan-2,5-diol 
• 79124-66-6 N-(methanesulfonyl)-16-(m-chlorophenoxy)-ω-tetranor-PGE₂-carboxamide 
• 101915-58-6 (3aR,4R,5R,6aS)-4-[(E)-(R)-4-(3-Chloro-phenoxy)-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one 
• 121221-70-3 methyl 2-<(1SR, 3SR, 5RS, 6RS, 7RS)-7-tert-butyldimethylsilyloxy-6-<(3RS)-3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1(E)-en-1-yl>-2-oxabicyclo<3.3.0>oct-3-yl>acetate 
• 109323-21-9 (1SR,2RS,3RS,4RS)-3-<(3SR)-4-(3-chlorophenoxy)-3-(1-ethoxy-ethoxy)-1(E)-butenyl>-2-<3-cyano-3-dimethylamino-2(E)-propenyl>-4-(1-ethoxy-ethoxy)cyclopentanol 
• 109323-21-9 (1SR,2RS,3RS,4RS)-3-<(3SR)-4-(3-chlorophenoxy)-3-(1-ethoxy-ethoxy)-1(E)-butenyl>-2-<3-cyano-3-dimethylamino-2(Z)-propenyl>-4-(1-ethoxy-ethoxy)cyclopentanol 
• 121221-69-0 (1SR, 5RS, 6RS, 7RS)-7-tert-butyldimethylsilyloxy-6-<(3RS)-3-tert-butyldimethylsilyloxy-4-(3-chlorophenoxy)but-1(E)-en-1-yl>-2-oxabicyclo<3.3.0>octan-3ξ-ol 
• 109323-20-8 (1SR,5RS,6RS,7RS)-6-<(3SR)-4-(3-chlorophenoxy)-3-(1-ethoxy-ethoxy)-1(E)-butenyl>-7-(1-ethoxy-ethoxy)-2-oxabicyclo<3.3.0>octan-3ξ-ol 

Relevant academic research and scientific papers

An improved and efficient process for the preparation of (+)-cloprostenol

Abstract An improved and efficient synthesis of (+)-cloprostenol has been accomplished in nine steps and 26% overall yield from commercially available (-)-Corey lactone 4-phenylbenzoate alcohol 1. The present route avoids tedious purifications and require

PROSTANOIDS. XXVII. SOME ASPECTS OF CHEMO- AND STEREOSELECTIVE REDUCTION OF 7α-HYDROXY-6β-(3-OXO-4-m-CHLOROPHENOXY-1E-BUTENYL)-2-OXABICYCLOOCTAN-3-ONE

The chemoselective reduction of 7α-hydroxy-6β-(3-oxo-4-m-chlorophenoxy-1E-butenyl)-2-oxabicyclooctan-3-one with respect to the oxo group was studied by means of readily obtainable reagents based on boron and aluminum.The optimum stereoselectivity of reduction was obtained with the use of diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide in methylene chloride at -78 deg C.

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).