54713-44-9 Usage
Description
[1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclopent a[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R),5b,6aa]] is a complex organic compound with a unique molecular structure. It is characterized by its biphenyl core, a chlorophenoxy group, and a hexahydro-2-oxo-2H-cyclopent a[b]furan-5-yl ester moiety. [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclop enta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R),5b,6aa]] is known for its potential applications in the pharmaceutical industry, particularly in the synthesis of prostaglandin analogues.
Uses
Used in Pharmaceutical Industry:
[1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclopent a[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R),5b,6aa]] is used as a reagent in the synthesis of (+)-cloprostenol, a synthetic analogue of prostoglandin F2α. Prostaglandins are a group of naturally occurring lipid compounds that have various physiological effects, including the promotion of smooth muscle contraction, vasodilation, and regulation of inflammation. [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclop enta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R),5b,6aa]] plays a crucial role in the development of new drugs targeting these physiological processes.
Used in Synthesis of Prostaglandin Analogues:
In the field of medicinal chemistry, [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclopent a[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R),5b,6aa]] is utilized as a key intermediate in the synthesis of prostaglandin F2α analogues. These analogues have potential applications in treating various medical conditions, such as cardiovascular diseases, inflammation, and reproductive disorders. [1,1'-Biphenyl]-4-carboxylic acid, 4-[4-(3-chlorophenoxy)-3-hydroxy-1-butenyl]hexahydro-2-oxo-2H-cyclop enta[b]furan-5-yl ester, [3aR-[3aa,4a(1E,3R),5b,6aa]]'s unique structure allows for the development of new drugs with improved efficacy and reduced side effects.
Check Digit Verification of cas no
The CAS Registry Mumber 54713-44-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,4,7,1 and 3 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 54713-44:
(7*5)+(6*4)+(5*7)+(4*1)+(3*3)+(2*4)+(1*4)=119
119 % 10 = 9
So 54713-44-9 is a valid CAS Registry Number.
54713-44-9Relevant articles and documents
A unified strategy to prostaglandins: chemoenzymatic total synthesis of cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost guided by biocatalytic retrosynthesis
Chen, Fener,Huang, Zedu,Jiang, Meifen,Li, Weijian,Tang, Pei,Ye, Baijun,Zhang, Guo-Tai,Zhu, Kejie
, p. 10362 - 10370 (2021/08/16)
Development of efficient and stereoselective synthesis of prostaglandins (PGs) is of utmost importance, owing to their valuable medicinal applications and unique chemical structures. We report here a unified synthesis of PGs cloprostenol, bimatoprost, PGF2α, fluprostenol, and travoprost from the readily available dichloro-containing bicyclic ketone6aguided by biocatalytic retrosynthesis, in 11-12 steps with 3.8-8.4% overall yields. An unprecedented Baeyer-Villiger monooxygenase (BVMO)-catalyzed stereoselective oxidation of6a(99% ee), and a ketoreductase (KRED)-catalyzed diastereoselective reduction of enones12(87?:?13 to 99?:?1 dr) were utilized in combination for the first time to set the critical stereochemical configurations under mild conditions. Another key transformation was the copper(ii)-catalyzed regioselectivep-phenylbenzoylation of the secondary alcohol of diol10(9.3?:?1 rr). This study not only provides an alternative route to the highly stereoselective synthesis of PGs, but also showcases the usefulness and great potential of biocatalysis in construction of complex molecules.
N-(Methanesulfonyl)-16-phenoxyprostaglandincarboxamides: Tissue-Selective, Uterine Stimulants
Schaaf, Thomas K.,Bindra, Jasjit S.,Eggler, James F.,Plattner, Jacob J.,Nelson, A. James,et al.
, p. 1353 - 1359 (2007/10/02)
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).