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

Base Information

Chemical Name:tert-butyl{[(2E)-2-((3S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-fluoro-2-methylenecyclohexylidene)ethyl]oxy}diphenylsilane
CAS No.:905976-91-2
Molecular Formula:C₃₁H₄₅FO₂Si₂
Molecular Weight:524.867
Hs Code.:

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

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Chemical Property of tert-butyl{[(2E)-2-((3S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-fluoro-2-methylenecyclohexylidene)ethyl]oxy}diphenylsilane

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Technology Process of tert-butyl{[(2E)-2-((3S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-fluoro-2-methylenecyclohexylidene)ethyl]oxy}diphenylsilane

There total 10 articles about tert-butyl{[(2E)-2-((3S,5R)-5-{[tert-butyl(dimethyl)silyl]oxy}-3-fluoro-2-methylenecyclohexylidene)ethyl]oxy}diphenylsilane 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: 47.0%

: 905976-86-5
tert-butyl[((2E)-2-{(5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-[(trimethylsilyl)methyl]cyclohex-2-en-1-ylidene}ethyl)oxy]diphenylsilane

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

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

Guidance literature:: With sodium hydrogencarbonate; Selectfluor; In acetonitrile; at 20 ℃; for 1.5h;
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

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

Guidance literature:: Multi-step reaction with 3 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

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

Reference yield:

: 905976-88-7
(4S)-4-{[tert-butyl(dimethyl)silyl]oxy}-2-(2-{[tert-butyl(diphenyl)silyl]oxy}-1-hydroxyethyl)cyclohexanone

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

Guidance literature:: Multi-step reaction with 5 steps

1.1: 87 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

2.1: 64 percent / DBU / tetrahydrofuran / 3 h / 20 °C

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

3.2: 60 percent / tetrahydrofuran; hexane / 3.5 h / -40 °C

4.1: 98 percent / LiCl / (Ph₃P)4Pd / tetrahydrofuran / 2 h / 20 °C

5.1: 47 percent / NaHCO₃; Selectfluor^TM / acetonitrile / 1.5 h / 20 °C

With sodium hydrogencarbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; Selectfluor; triethylamine; lithium chloride; lithium diisopropyl amide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;
DOI:10.1021/jo060516m