2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-cyclohex-(Z)-ylidene]-ethanol

Base Information

Chemical Name:2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-cyclohex-(Z)-ylidene]-ethanol
CAS No.:446867-33-0
Molecular Formula:C₂₂H₄₆O₃Si₂
Molecular Weight:414.776
Hs Code.:

Synonyms:2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-cyclohex-(Z)-ylidene]-ethanol

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Chemical Property of 2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-cyclohex-(Z)-ylidene]-ethanol

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Technology Process of 2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-cyclohex-(Z)-ylidene]-ethanol

There total 7 articles about 2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-cyclohex-(Z)-ylidene]-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: 46.0%

: 446867-15-8
[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-cyclohex-(Z)-ylidene]-acetic acid ethyl ester

: 446867-33-0
2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-cyclohex-(Z)-ylidene]-ethanol

Guidance literature:: With diisobutylaluminium hydride; In diethyl ether; hexane; at -78 - 20 ℃;
DOI:10.1016/S0968-0896(02)00058-5

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

: 446867-33-0
2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-cyclohex-(Z)-ylidene]-ethanol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2.1: LDA / tetrahydrofuran; hexane / 0.25 h / -78 °C

2.2: 50 percent / PhSeCl; 1 N aq. HCl / CH₂Cl₂; tetrahydrofuran / -78 - 20 °C

3.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: tetrahydrofuran; hexane / 12 h / -78 - -30 °C

3.3: 27 percent / NaBH₄ / methanol

4.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / -30 °C

5.1: 92 percent / m-CPBA / CH₂Cl₂

6.1: 100 percent / benzene / 6 h / Heating

7.1: 46 percent / DIBAL-H / diethyl ether; hexane / -78 - 20 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene; 3.2: Michael addition;
DOI:10.1016/S0968-0896(02)00058-5

Reference yield:

: 61447-86-7
(S)-3-hydroxy-2,2-dimethylcyclohexanone

: 446867-33-0
2-[(3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-4,4-dimethyl-cyclohex-(Z)-ylidene]-ethanol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2.1: LDA / tetrahydrofuran; hexane / 0.25 h / -78 °C

2.2: 50 percent / PhSeCl; 1 N aq. HCl / CH₂Cl₂; tetrahydrofuran / -78 - 20 °C

3.1: LDA / tetrahydrofuran; hexane / 0.5 h / -78 °C

3.2: tetrahydrofuran; hexane / 12 h / -78 - -30 °C

3.3: 27 percent / NaBH₄ / methanol

4.1: 88 percent / 2,6-lutidine / CH₂Cl₂ / -30 °C

5.1: 92 percent / m-CPBA / CH₂Cl₂

6.1: 100 percent / benzene / 6 h / Heating

7.1: 46 percent / DIBAL-H / diethyl ether; hexane / -78 - 20 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene; 3.2: Michael addition;
DOI:10.1016/S0968-0896(02)00058-5