(5S,6R,7E,9E,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxahexadeca-7,9,13-trien-11-ynoic acid, t-butyl ester

Base Information

Chemical Name:(5S,6R,7E,9E,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxahexadeca-7,9,13-trien-11-ynoic acid, t-butyl ester
CAS No.:524714-15-6
Molecular Formula:C₂₅H₃₁FO₇
Molecular Weight:462.515
Hs Code.:

Synonyms:(5S,6R,7E,9E,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxahexadeca-7,9,13-trien-11-ynoic acid, t-butyl ester

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Chemical Property of (5S,6R,7E,9E,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxahexadeca-7,9,13-trien-11-ynoic acid, t-butyl ester

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Technology Process of (5S,6R,7E,9E,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxahexadeca-7,9,13-trien-11-ynoic acid, t-butyl ester

There total 9 articles about (5S,6R,7E,9E,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxahexadeca-7,9,13-trien-11-ynoic acid, t-butyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 58.0%

: 524714-14-5
1,1-dimethylethyl [[(2S,3R)-3-[(1E,3E,7E,9S)-10-(4-fluorophenoxy)-9-hydroxyl-1,3,7-decatrien-5-ynyl]-1,4-dioxaspiro[4,5]dec-2-yl]methoxy]ethanoate

: 524714-15-6
(5S,6R,7E,9E,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxahexadeca-7,9,13-trien-11-ynoic acid, t-butyl ester

Guidance literature:: With acetic acid; In ethyl acetate; at 55 ℃; for 20h;
DOI:10.1021/jm030569l

Reference yield:

: 5292-43-3
bromoacetic acid tert-butyl ester

: 524714-15-6
(5S,6R,7E,9E,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxahexadeca-7,9,13-trien-11-ynoic acid, t-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: 44 percent / aq. NaOH; tetrabutylammonium sulfate / toluene / 16 h

2.1: 92 percent / aq. NaIO₄ / acetone / 4 h

3.1: n-BuLi / tetrahydrofuran; hexane / -30 - 0 °C

3.2: 49 percent / tetrahydrofuran; hexane / 1 h / -30 °C

4.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h

5.1: 50 percent / tetrakistriphenylphosphine-Pd⁽⁰⁾; CuI; diethylamine / tetrahydrofuran / 2 h

6.1: 58 percent / AcOH / ethyl acetate / 20 h / 55 °C

With sodium hydroxide; sodium periodate; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; tetrabutyl ammonium fluoride; acetic acid; tetrabutylammonium sulfate; diethylamine; In tetrahydrofuran; hexane; ethyl acetate; acetone; toluene; 5.1: Sonogashira coupling;
DOI:10.1021/jm030569l

Reference yield:

: 524714-06-5
(1E,3S)-1-bromo-4-(4-fluorophenoxy)-3-hydroxy-1-butene

: 524714-15-6
(5S,6R,7E,9E,13E,15S)-16-(4-fluorophenoxy)-5,6,15-trihydroxy-3-oxahexadeca-7,9,13-trien-11-ynoic acid, t-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 50 percent / tetrakistriphenylphosphine-Pd⁽⁰⁾; CuI; diethylamine / tetrahydrofuran / 2 h

2: 58 percent / AcOH / ethyl acetate / 20 h / 55 °C

With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; acetic acid; diethylamine; In tetrahydrofuran; ethyl acetate; 1: Sonogashira coupling;
DOI:10.1021/jm030569l