81845-98-9

Basic information

• Product Name: 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester
• Synonyms: 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester
• CAS NO: 81845-98-9
• Molecular Weight: 404.547
• Mol File: 81845-98-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 558.3±50.0 °C(Predicted)
• Density: 1.116±0.06 g/cm3(Predicted)
• CAS DataBase Reference: 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester(81845-98-9)
• EPA Substance Registry System: 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester(81845-98-9)

Safety Data

• Hazardous Substances Data: 81845-98-9(Hazardous Substances Data)

Usage

Description

2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester is a complex organic compound with a unique molecular structure. It is characterized by its hexahydro-1H-cyclopenta[b]naphthalene core, which is substituted with various functional groups, including hydroxy and ester groups. 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester exhibits a range of biological activities and has potential applications in various industries.

Uses

Used in Pharmaceutical Industry:
2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester is used as a pharmaceutical agent for the treatment of pulmonary arterial hypertension (PAH). It functions as an impurity of Treprostinil (T719500), a synthetic analog of Prostacyclin (P839060), which is a medication marketed under the trade name Remodulin. 2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester exhibits antihypertensive properties and helps in managing the symptoms of PAH.
Used in Drug Delivery Systems:
2-((1R,2R,3aS,9aS)-2-hydroxy-1-(S)-3-hydroxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-5-yloxylacetic acid methyl ester can also be employed in drug delivery systems to improve the bioavailability and therapeutic outcomes of various drugs. Its unique molecular structure allows for the development of novel drug delivery systems, such as organic and metallic nanoparticles, which can enhance the delivery and efficacy of the compound in treating specific medical conditions.

Upstream product

• 40359-32-8 3-allyloxy-benzaldehyde 
• 96-32-2 bromoacetic acid methyl ester 
• 101692-02-8 (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol 
• 100-83-4 meta-hydroxybenzaldehyde 
• 79950-42-8 2-allyl-3-hydroxy-benzaldehyde 
• 1355990-13-4 (S)-1-[2-allyl-3-(4-methoxybenzyloxy)phenyl]-6-benzyloxyundec-2-yn-1-ol 
• 1355990-15-6 (S)-1-[2-allyl-3-(4-methoxybenzyloxy)phenyl]-6-benzyloxyundec-2-yn-1-one 
• 1355990-17-8 (1R,6S)-1-[-2-allyl-3-(4-methoxybenzyloxy)phenyl]-6-benzyloxyundec-2-yn-1-ol 
• 1355990-19-0 {(1R,6S)-1-[-2-allyl-3-(4-methoxybenzyloxy)phenyl]-6-benzyloxyundec-2-ynyloxy}-tert-butyl-dimethyl-silane 
• 1355990-21-4 (4R,9aS)-3-((S)-3-benzyloxyoctyl)-4-(tert-butyldimethylsilanyloxy)-8-(4-methoxybenzyloxy)-1,4,9,9a-tetrahydrocyclopenta[b]napthalen-2-one 
• 1355990-23-6 (3aS,9aS)-1-((S)-3-benzyloxyoctyl)-5-hydroxy-1,3,3a,4,9,9a-hexahydrobenz[f]inden-2-one 
• 1355990-25-8 (1R,2R,3aS,9aS)-1-((S)-3-benzyloxyoctyl)-2,3,3a,4,9,9a-hexahydro-1H-cyclopenta[b]naphthalene-2,5-diol 
• 1355990-09-8 2-allyl-3-(4-methoxybenzyloxy)benzaldehyde 
• 67-56-1 methanol 

Downstream Products

• 81846-19-7 treprostinil 

Relevant articles and documents

Process for Preparing Treprostinil and Intermediate Therefor

The present invention relates to a synthesis method of high-purity treprostinil, and an intermediate for the same. According to the synthesis method of the present invention, high-purity treprostinil can be synthesized in an economical and efficient manner by using intramolecular Friedel-Crafts allylic alkylation. Accordingly, the synthesis method of the present invention may be effectively used for commercial mass-production of treprostinil.COPYRIGHT KIPO 2017

COMPOUNDS AND METHODS FOR DELIVERY OF PROSTACYCLIN ANALOGS

This invention pertains generally to prostacyclin formulations and methods for their use in promoting vasodilation, inhibiting platelet aggregation and thrombus formation, stimulating thrombolysis, inhibiting cell proliferation (including vascular remodeling), providing cytoprotection, preventing atherogenesis and inducing angiogenesis.

SYNTHESIS OF TREPROSTINIL AND INTERMEDIATES USEFUL THEREIN

Treprostinil is prepared by a process which involves Pauson - Khan cyclization of an an alkene-substituted, alkyne-substituted benzene corresponding to formula : (I) where PMB represents para-methoxy benzyl protecting group and R1 and R2 are alcohol protecting groups. Following cyclization, the resulting compound can be subjected to several chemical transformations followed by alkylation, hydrolysis and salt formation to yield treprostinil sodium. The use of para-methoxybenzyl group as the phenolic protecting group confers several process advantages that result in simplified purification of the final product and improved yields.