913258-19-2

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 
• 124988-64-3 (S)-4-phenyl-1,2-butanediol 
• 1449-46-3 benzyltriphenylphosphonium bromide 
• 768-56-9 4-Phenylbut-1-ene 
• 994-30-9 triethylsilyl chloride 
• 118629-73-5 (S)-2-hydroxy-4-phenylbutyl 4-methylbenzenesulfonate 

Downstream Products

• 913258-22-7 (S)-1,2-epoxy-4-phenylbutane 
• 41639-83-2 latanoprost acid 
• 913258-32-9 (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 
• 145773-22-4 isopropyl (E)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(R)-3-hydroxy-5-phenylpentyl]cyclopentyl}hept-5-enoate 
• 913258-23-8 (S)-2-hydroxy-1-iodo-4-phenylbutane 
• 913258-20-5 (S)-4-phenyl-1-iodo-2-(triethylsiloxy)butane 

Relevant academic research and scientific papers

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.

PROCESS FOR PREPARATION OF 13,14-DIHYDRO-PGF2α DERIVATIVES

Invention relates to the process for preparation of 13,14-dihydro-PGF2α derivatives of R or S configuration at carbon atom in omega chain substituted by hydroxyl, represented by formula (I), wherein the meaning of substituents is defined in the description. Compounds (I) are valuable biologically active substances or intermediates thereof. The invention especially relates to the process for preparation of 13,14-dihydro-15(R)-17-substituted-18,19,20-trinor-PGF2α, ie. latanoprost.