(1S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-[2-chloro-eth-(E)-ylidene]-2-methylene-cyclohexane

Base Information

Chemical Name:(1S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-[2-chloro-eth-(E)-ylidene]-2-methylene-cyclohexane
CAS No.:142508-76-7
Molecular Formula:C₂₂H₄₃ClO₂Si₂
Molecular Weight:431.206
Hs Code.:

Synonyms:(1S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-[2-chloro-eth-(E)-ylidene]-2-methylene-cyclohexane

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Chemical Property of (1S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-[2-chloro-eth-(E)-ylidene]-2-methylene-cyclohexane

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Technology Process of (1S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-[2-chloro-eth-(E)-ylidene]-2-methylene-cyclohexane

There total 22 articles about (1S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-[2-chloro-eth-(E)-ylidene]-2-methylene-cyclohexane 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: 79.0%

: 142508-75-6
2-[(3S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-(tert-butyl-dimethyl-silanyloxymethyl)-2-methylene-cyclohex-(E)-ylidene]-ethanol

: 142508-76-7
(1S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-[2-chloro-eth-(E)-ylidene]-2-methylene-cyclohexane

Guidance literature:: With N-chloro-succinimide; dimethylsulfide; In dichloromethane; at -20 - 25 ℃; for 1.08333h;
DOI:10.1021/jm00095a026

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 142508-76-7
(1S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-[2-chloro-eth-(E)-ylidene]-2-methylene-cyclohexane

Guidance literature:: Multi-step reaction with 6 steps

1: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h

2: 87 percent / DIBAL-H / toluene / 2 h / -78 - 25 °C

3: 65 percent / 2,4,6-trimethylbenzoic acid / CH₂Cl₂ / 12.5 h / 135 - 145 °C

4: 87 percent / 9-fluorenone, tert-butyl methyl ether / 16 h / Irradiation

5: 51 percent / DIBAL-H / toluene; hexane / 2 h / 0 °C

6: 79 percent / NCS, dimethyl sulfide / CH₂Cl₂ / 1.08 h / -20 - 25 °C

With 2,6-dimethylpyridine; N-chloro-succinimide; 9-fluorenone; dimethylsulfide; tert-butyl methyl ether; mesitylenecarboxylic acid; diisobutylaluminium hydride; In hexane; dichloromethane; toluene;
DOI:10.1021/jm00095a026

Reference yield:

: 19978-32-6
3-bromo-2H-pyran-2-one

: 142508-76-7
(1S,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-1-(tert-butyl-dimethyl-silanyloxymethyl)-3-[2-chloro-eth-(E)-ylidene]-2-methylene-cyclohexane

Guidance literature:: Multi-step reaction with 8 steps

2: 1.) tributyltin hydride, AIBN, DBU / 1.) benzene, reflux, 2 h, 2.) THF, -35 deg C - 25 deg C, 11 h

3: 86 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h

4: 87 percent / DIBAL-H / toluene / 2 h / -78 - 25 °C

5: 65 percent / 2,4,6-trimethylbenzoic acid / CH₂Cl₂ / 12.5 h / 135 - 145 °C

6: 87 percent / 9-fluorenone, tert-butyl methyl ether / 16 h / Irradiation

7: 51 percent / DIBAL-H / toluene; hexane / 2 h / 0 °C

8: 79 percent / NCS, dimethyl sulfide / CH₂Cl₂ / 1.08 h / -20 - 25 °C

With 2,6-dimethylpyridine; N-chloro-succinimide; 9-fluorenone; dimethylsulfide; 2,2'-azobis(isobutyronitrile); tert-butyl methyl ether; mesitylenecarboxylic acid; tri-n-butyl-tin hydride; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In hexane; dichloromethane; toluene;
DOI:10.1021/jm00095a026