[3S-(1E,3β,5α)]-[3-fluoro-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethanol

Base Information

Chemical Name:[3S-(1E,3β,5α)]-[3-fluoro-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethanol
CAS No.:367487-78-3
Molecular Formula:C₁₅H₂₇FO₂Si
Molecular Weight:286.462
Hs Code.:

Synonyms:[3S-(1E,3β,5α)]-[3-fluoro-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethanol

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Chemical Property of [3S-(1E,3β,5α)]-[3-fluoro-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethanol

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Technology Process of [3S-(1E,3β,5α)]-[3-fluoro-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethanol

There total 15 articles about [3S-(1E,3β,5α)]-[3-fluoro-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethanol 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: 100.0%

: 367487-77-2
tert-butyl (2E)-2-[(3S,5R)-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-3-fluoro-2-methylene-cyclohexylidene]acetate

: 367487-78-3
[3S-(1E,3β,5α)]-[3-fluoro-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethanol

Guidance literature:: With diisobutylaluminium hydride; In tetrahydrofuran; at -60 - -42 ℃; for 7.5h;
DOI:10.1021/jo015788y

Reference yield: 91.0%

: 905976-91-2
tert-butyl{[(2E)-2-((3S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-fluoro-2-methylenecyclohexylidene)ethyl]oxy}diphenylsilane

: 367487-78-3
[3S-(1E,3β,5α)]-[3-fluoro-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethanol

Guidance literature:: With potassium hydroxide; In methanol; at 70 ℃; for 19h;
DOI:10.1021/jo060516m

Reference yield:

: 905976-87-6
(2E,4S)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(2-{[tert-butyl(diphenyl)silyl]oxy}ethylidene)cyclohexanone

: 367487-78-3
[3S-(1E,3β,5α)]-[3-fluoro-5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethanol

Guidance literature:: Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: 60 percent / tetrahydrofuran; hexane / 3.5 h / -40 °C

2.1: 98 percent / LiCl / (Ph₃P)4Pd / tetrahydrofuran / 2 h / 20 °C

3.1: 47 percent / NaHCO₃; Selectfluor^TM / acetonitrile / 1.5 h / 20 °C

4.1: 91 percent / KOH / methanol / 19 h / 70 °C

With potassium hydroxide; sodium hydrogencarbonate; Selectfluor; lithium chloride; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; acetonitrile;
DOI:10.1021/jo060516m