Cyclohexanone, 4-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2-ethyl-2-(hydroxymethyl) -, (2S,4R)-

Base Information

Chemical Name:Cyclohexanone, 4-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2-ethyl-2-(hydroxymethyl) -, (2S,4R)-
CAS No.:410071-90-8
Molecular Formula:C26H36O3Si
Molecular Weight:424.656
Hs Code.:

Synonyms:

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Chemical Property of Cyclohexanone, 4-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2-ethyl-2-(hydroxymethyl) -, (2S,4R)-

Chemical Property:

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Technology Process of Cyclohexanone, 4-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2-ethyl-2-(hydroxymethyl) -, (2S,4R)-

There total 12 articles about Cyclohexanone, 4-[[[(1,1-dimethylethyl)diphenylsilyl]oxy]methyl]-2-ethyl-2-(hydroxymethyl) -, (2S,4R)- 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: 66.4%

: 410071-89-5
(3aR,5R)-5-(tert-butyldiphenylsilyloxymethyl)-3a-ethyl-3,3a,4,5,6,7-hexahydrobenz[c]isoxazole

: 410071-90-8
(2S,4R)-4-(tert-butyldiphenylsilyloxymethyl)-2-ethyl-2-(hydroxymethyl)cyclohexanone

Guidance literature:: With acetic acid; zinc; at 20 ℃; for 4h;
DOI:10.1021/ja0177049

Reference yield:

: 4435-54-5
2-Methylene-1-butanol

: 410071-90-8
(2S,4R)-4-(tert-butyldiphenylsilyloxymethyl)-2-ethyl-2-(hydroxymethyl)cyclohexanone

Guidance literature:: Multi-step reaction with 11 steps

1: EtCO₂H / 135 °C

2: 247.5 g / KOH / ethanol; H₂O / 20 °C

3: Et₃N / diethyl ether / 0.67 h / 0 °C

4: 51.0 g / n-BuLi / tetrahydrofuran; various solvent(s) / 1.33 h / -78 - 0 °C

5: 70.4 percent / titanium tetraisopropoxide; i-Pr₂NEt; titanium tetrachloride / CH₂Cl₂ / 9 h / 0 °C

6: 45.85 percent / NaBH₄ / tetrahydrofuran; H₂O / 12 h / 20 °C

7: 91.5 percent / imidazole / dimethylformamide / 1 h / 20 °C

8: DIBAL / CH₂Cl₂; toluene / 0.33 h / -78 °C

9: H₂NOH*HCl; NaOAc / ethanol / 1 h / 20 °C

10: 20.0 g / aq. NaClO / CH₂Cl₂ / 3.5 h / 20 °C

11: 66.4 percent / Zn; AcOH / 4 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; potassium hydroxide; sodium hypochlorite; sodium tetrahydroborate; n-butyllithium; hydroxylamine hydrochloride; sodium acetate; titanium tetrachloride; diisobutylaluminium hydride; acetic acid; propionic acid; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: Claisen-Johnson rearrangement;
DOI:10.1021/ja0177049

Reference yield:

: 13722-73-1
4-ethylpent-4-enoic acid

: 410071-90-8
(2S,4R)-4-(tert-butyldiphenylsilyloxymethyl)-2-ethyl-2-(hydroxymethyl)cyclohexanone

Guidance literature:: Multi-step reaction with 9 steps

1: Et₃N / diethyl ether / 0.67 h / 0 °C

2: 51.0 g / n-BuLi / tetrahydrofuran; various solvent(s) / 1.33 h / -78 - 0 °C

3: 70.4 percent / titanium tetraisopropoxide; i-Pr₂NEt; titanium tetrachloride / CH₂Cl₂ / 9 h / 0 °C

4: 45.85 percent / NaBH₄ / tetrahydrofuran; H₂O / 12 h / 20 °C

5: 91.5 percent / imidazole / dimethylformamide / 1 h / 20 °C

6: DIBAL / CH₂Cl₂; toluene / 0.33 h / -78 °C

7: H₂NOH*HCl; NaOAc / ethanol / 1 h / 20 °C

8: 20.0 g / aq. NaClO / CH₂Cl₂ / 3.5 h / 20 °C

9: 66.4 percent / Zn; AcOH / 4 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; sodium hypochlorite; sodium tetrahydroborate; n-butyllithium; hydroxylamine hydrochloride; sodium acetate; titanium tetrachloride; diisobutylaluminium hydride; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja0177049