1-<(S)-5-(tert-Butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl>-3,3-(ethylenedioxy)butane

Base Information

Chemical Name:1-<(S)-5-(tert-Butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl>-3,3-(ethylenedioxy)butane
CAS No.:172788-51-1
Molecular Formula:C₂₁H₄₀O₃Si
Molecular Weight:368.632
Hs Code.:

Synonyms:1-<(S)-5-(tert-Butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl>-3,3-(ethylenedioxy)butane

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Chemical Property of 1-<(S)-5-(tert-Butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl>-3,3-(ethylenedioxy)butane

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Technology Process of 1-<(S)-5-(tert-Butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl>-3,3-(ethylenedioxy)butane

There total 2 articles about 1-<(S)-5-(tert-Butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl>-3,3-(ethylenedioxy)butane 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: 98.0%

: (S)-3-(tert-Butyl-dimethyl-silanyloxy)-2,2,6-trimethyl-1-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-cyclohexanol

: 172788-51-1
1-<(S)-5-(tert-Butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl>-3,3-(ethylenedioxy)butane

Guidance literature:: With thionyl chloride; In pyridine; at -10 ℃; for 0.166667h;

Reference yield:

: 106540-32-3
(3S)-3-t-butyldimethylsilyloxy-2,2,6-trimethylcyclohexanone

: 172788-51-1
1-<(S)-5-(tert-Butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl>-3,3-(ethylenedioxy)butane

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) Mg, 1,2-dibromoethane / 1.) THF, 25 deg C, 1 h, 2.) THF, r.t., 15 h

2: 98 percent / SOCl₂ / pyridine / 0.17 h / -10 °C

With thionyl chloride; magnesium; ethylene dibromide; In pyridine;

Reference yield:

: 172788-51-1
1-<(S)-5-(tert-Butyldimethylsilyloxy)-2,6,6-trimethylcyclohex-1-en-1-yl>-3,3-(ethylenedioxy)butane

: 149051-08-1
C₃₆H₄₆O₄S₂

Guidance literature:: Multi-step reaction with 20 steps

1: nBu₄NF / tetrahydrofuran / 1.) 40 deg C, 20 h, 2.) r.t., 48 h

2: KH / tetrahydrofuran / 1.) r.t., 0.5 h, 2.) r.t., 1 h

3: 99 percent / p-TsOH*H₂O / acetone; H₂O / 4 h / Heating

4: 79 percent / NaH, MeOH / 16 h / Heating

5: 18 percent / SnCl₄ / CH₂Cl₂; H₂O / 1.) 0 deg C, 1 h, 2.) r.t., 4 h

6: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h

7: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h

8: 88 percent / DIBAL / toluene / 0.5 h / -78 °C

9: Et₃N / CH₂Cl₂ / 0.5 h / -78 °C

10: LiBr / tetrahydrofuran; CH₂Cl₂ / 1 h / -20 °C

11: NaH, n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1.) 0 deg C, 15 min; 0 deg C, 30 min, 2.) -20 deg C, 15 h

12: 31 percent / SnCl₄ / CH₂Cl₂; H₂O / 2 h / 0 °C

13: NaH / tetrahydrofuran / 1.) reflux, 1 h, 2.) r.t., 1 h

14: 1.) CuI / 1.) ether, -20 deg C, 10 min, 2.) ether, -78 deg C, 0.5 h; -20 deg C, 15 h

15: 94 percent / DIBAL / toluene / 1 h / -78 °C

16: 99 percent / pyridine, DMAP / 0.5 h / 0 °C

17: 1.) n-BuLi, Me₃SnCl, 2.) LiCl / 2.) Pd(dba)2 / 1.) THF, hexane, -50 deg C, 0.5 h; -50 deg C, 3 h, 2.) DMF, 100 deg C, 4 h

18: 71 percent / CrO₃, 3,5-dimethylpyrazole / CH₂Cl₂ / 0.5 h / -20 °C

19: 43 percent / BBr₃ / CH₂Cl₂ / 2.5 h / -78 - -10 °C

20: 62 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / Ambient temperature

With pyridine; 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; methanol; dmap; copper(l) iodide; n-butyllithium; boron trifluoride diethyl etherate; trimethyltin(IV)chloride; tetrabutyl ammonium fluoride; boron tribromide; tin(IV) chloride; potassium hydride; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; lithium chloride; lithium bromide; bis(dibenzylideneacetone)-palladium⁽⁰⁾; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; dichloromethane; water; acetone; toluene;