301834-95-7

Upstream product

• 123-20-6 vinyl n-butyrate 
• 88462-65-1 (+/-)-4-[(3-trifluoromethyl)phenoxy]-1-butyne-3-ol 
• 124-63-0 methanesulfonyl chloride 
• 63212-89-5 (3-trifluoromethylphenoxy)acetaldehyde 
• 4301-14-8 acetylenemagnesium bromide 
• 443361-68-0 Methanesulfonic acid (S)-1-(3-trifluoromethyl-phenoxymethyl)-prop-2-ynyl ester 
• 107-92-6 butyric acid 
• 63212-88-4 (3-trifluoromethylphenoxy)acetaldehyde diethyl acetal 
• 98-17-9 3-Trifluoromethylphenol 

Downstream Products

• 443361-68-0 Methanesulfonic acid (S)-1-(3-trifluoromethyl-phenoxymethyl)-prop-2-ynyl ester 
• 301834-98-0 (R)-tert-butyldimethyl((1-(3-(trifluoromethyl)phenoxy)but-3-yn-2-yl)oxy)silane 
• 301834-96-8 (3R)-4-[3-(trifluoromethyl)phenoxy]-3-hydroxy-1-butyne 

Relevant academic research and scientific papers

Synthesis of the potent antiglaucoma agent, travoprost

A commercial synthesis of the antiglaucoma agent, travoprost 2, is described. A total of 22 synthetic steps are required to provide the single enantiomer prostanoid, with the longest linear sequence being 16 steps from 3-hydroxybenzotrifluoride. The route is based upon a cuprate-mediated coupling of the single enantiomer vinyl iodide 13 and the tricyclic ketone 5, of high stereochemical purity, to yield the single isomer bicyclic ketone 15. A Baeyer - Villiger oxidation provides the lactone 16 as a crystalline solid, thus limiting the need for chromatographic purification. DIBAL-H reduction, Wittig reaction, esterification, and silyl group deprotection complete the synthesis of travoprost.

An Enantioconvergent Synthesis of (R)-4-Aryloxy-1-butyne-3-ols for Prostanoid Side Chains

The single enantiomer title alcohols, useful as co-side chain precursors for pharmaceutically important prostaglandin analogues were synthesised from the corresponding racemic alcohols by a convenient 4-step sequence. After enzymatic acylation of the alco

Process for the preparation of prostaglandin precursors

A propargylic alcohol, enriched in the (R)-enantiomer, has the formula wherein R is C1-4 alkoxy, halogen, or C1-4 alkyl optionally substituted by OH or halogen. This is prepared by the steps of: (a) enantioselective (R)-esterification of the racemic alcohol using any acyl donor and a first enzyme; (b) removal of the untreated (S)-alcohol; and (c) enantioselective hydrolysis of the (R)-ester, using a second enzyme.