(4S,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-6-(2-{[tert-butyl(diphenyl)silyl]oxy}ethylidene)cyclohex-1-en-1-yl trifluoromethanesulfonate

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Chemical Name:(4S,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-6-(2-{[tert-butyl(diphenyl)silyl]oxy}ethylidene)cyclohex-1-en-1-yl trifluoromethanesulfonate
CAS No.:905976-90-1
Molecular Formula:C₃₁H₄₃F₃O₅SSi₂
Molecular Weight:640.912
Hs Code.:

Synonyms:(4S,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-6-(2-{[tert-butyl(diphenyl)silyl]oxy}ethylidene)cyclohex-1-en-1-yl trifluoromethanesulfonate

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Chemical Property of (4S,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-6-(2-{[tert-butyl(diphenyl)silyl]oxy}ethylidene)cyclohex-1-en-1-yl trifluoromethanesulfonate

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Technology Process of (4S,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-6-(2-{[tert-butyl(diphenyl)silyl]oxy}ethylidene)cyclohex-1-en-1-yl trifluoromethanesulfonate

There total 7 articles about (4S,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-6-(2-{[tert-butyl(diphenyl)silyl]oxy}ethylidene)cyclohex-1-en-1-yl trifluoromethanesulfonate 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:

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

: 905976-90-1
(4S,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-6-(2-{[tert-butyl(diphenyl)silyl]oxy}ethylidene)cyclohex-1-en-1-yl trifluoromethanesulfonate

Guidance literature:: Multi-step reaction with 3 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

With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo060516m

Reference yield:

: 905976-89-8
1-((5S)-5-{[tert-butyl(dimethyl)silyl]oxy}-2-oxocyclohexyl)-2-{[tert-butyl(diphenyl)silyl]oxy}ethyl methanesulfonate

: 905976-90-1
(4S,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-6-(2-{[tert-butyl(diphenyl)silyl]oxy}ethylidene)cyclohex-1-en-1-yl trifluoromethanesulfonate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 64 percent / DBU / tetrahydrofuran / 3 h / 20 °C

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

2.2: 60 percent / tetrahydrofuran; hexane / 3.5 h / -40 °C

With 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; In tetrahydrofuran; hexane;
DOI:10.1021/jo060516m

Reference yield:

: 55145-45-4
4-(tert-butyldimethylsilyloxy)cyclohexanone

: 905976-90-1
(4S,6E)-4-{[tert-butyl(dimethyl)silyl]oxy}-6-(2-{[tert-butyl(diphenyl)silyl]oxy}ethylidene)cyclohex-1-en-1-yl trifluoromethanesulfonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: BuLi; (+)-bis(α-methylbenzyl)amine hydrochloride / tetrahydrofuran / -100 - -78 °C

2.1: 39 percent / BF₃*OEt₂ / CH₂Cl₂ / 2 h / -78 °C

3.1: 87 percent / Et₃N / CH₂Cl₂ / 15 h / 20 °C

4.1: 64 percent / DBU / tetrahydrofuran / 3 h / 20 °C

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

5.2: 60 percent / tetrahydrofuran; hexane / 3.5 h / -40 °C

With n-butyllithium; (+)-bis(α-methylbenzyl)amine hydrochloride; boron trifluoride diethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium diisopropyl amide; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/jo060516m