913258-32-9

Basic information

• Product Name: (Z)-3-hydroxy-2-(hydroxymethyl)-2-methylpropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate
• Synonyms: (Z)-3-hydroxy-2-(hydroxymethyl)-2-methylpropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate
• CAS NO: 913258-32-9
• Molecular Weight: 492.653
• Mol File: 913258-32-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (Z)-3-hydroxy-2-(hydroxymethyl)-2-methylpropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-3-hydroxy-2-(hydroxymethyl)-2-methylpropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate(913258-32-9)
• EPA Substance Registry System: (Z)-3-hydroxy-2-(hydroxymethyl)-2-methylpropyl 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((R)-3-hydroxy-5-phenylpentyl)cyclopentyl)hept-5-enoate(913258-32-9)

Safety Data

• Hazardous Substances Data: 913258-32-9(Hazardous Substances Data)

Upstream product

• 157732-87-1 (4S)-2,2-dimethyl-4-(2-phenylethyl)-1,3-dioxolane 
• 152203-65-1 (4S)-2,2-dimethyl-4-styryl-1,3-dioxolane 
• 118629-73-5 (S)-2-hydroxy-4-phenylbutyl 4-methylbenzenesulfonate 
• 124988-64-3 (S)-4-phenyl-1,2-butanediol 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 768-56-9 4-Phenylbut-1-ene 
• 913258-19-2 (S)-4-phenyl-1-(p-tolylsulfonyloxy)-2-(triethylsiloxy)butane 
• 913258-20-5 (S)-4-phenyl-1-iodo-2-(triethylsiloxy)butane 
• 913258-17-0 1-<(Z)-6-{(1R,2R,3R,5S)-2-[(phenylsulfonyl)methyl]-3,5-bis(triethylsiloxy)cyclopentyl}hex-4-enyl>-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane 

Downstream Products

• 145773-22-4 isopropyl (E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate 
• 41639-83-2 latanoprost acid 

Relevant articles and documents

A new synthetic approach to high-purity (15R)-latanoprost

This paper describes a new synthesis of latanoprost (1) that afforded high purity latanoprost in 16.9 % overall yield in eight synthetic steps from sulfone 4. The "a chain" in a derivative of the (-)-"Corey lactone" was elongated first, followed by the attachment of a novel, enantiomerically pure "ω chain" synthon. This ensured the absence of the undesired (15S)-1 diastereomer in the synthesized prostaglandin. The crystalline nature of the novel sulfone 4 facilitated its purification. A variation of the new synthesis of latanoprost is described, where the laboratory-scale synthesis was further adapted to a hundred-gram scale. In the course of the present synthesis, a new prostaglandin sulfone intermediate, 21, which may find application in the synthesis of diverse prostaglandin analogs, was introduced. A practical synthesis of novel, enantiomerically pure "ω chain" synthons 15, 16, and 17 has also been carried out, employing diol 12, which was obtained from derivatives of the D-mannitol chiral pool. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.