6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-6-methyl-cyclohex-2-enone

Base Information

Chemical Name:6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-6-methyl-cyclohex-2-enone
CAS No.:331627-32-8
Molecular Formula:C₁₆H₃₀O₄Si
Molecular Weight:314.497
Hs Code.:

6-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-6-methyl-cyclohex-2-enone

Synonyms:6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-6-methyl-cyclohex-2-enone

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Chemical Property of 6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-6-methyl-cyclohex-2-enone

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Technology Process of 6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-6-methyl-cyclohex-2-enone

There total 1 articles about 6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-6-methyl-cyclohex-2-enone 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: 94.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 252979-17-2
(S)-6-hydroxymethyl-3-(methoxymethoxy)-6-methyl-2-cyclohexenone

: 331627-32-8
6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-6-methyl-cyclohex-2-enone

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 10h;
DOI:10.1021/jo0015772

Reference yield:

: 331627-32-8
6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-6-methyl-cyclohex-2-enone

: (2aS,3R,6R,8aR,8bS)-2a,3,4,6,7,8,8a,8b-octahydro-6-benzyloxymethyl-3,6-dimethyl-2a-(2-hydroxyethyl)-[1,8-bc]-naphtho-2-furanone

Guidance literature:: Multi-step reaction with 11 steps

1: 21.6 g / tetrahydrofuran / 6 h / 0 °C

2: 93 percent / Et₃N / benzene / 1 h / 20 °C

3: 8.75 g / DIBAL-H / toluene / 0.5 h / -78 °C

4: 97 percent / m-CPBA; Na₂HPO₄ / CHCl₃ / 0.5 h / -42 °C

5: 98 percent / DEAD; PPh₃ / tetrahydrofuran / 1 h / 20 °C

6: 89 percent / ethyl propiolate / pyridine; toluene / 8 h / Heating

7: 88 percent / CuI / diethyl ether / 0.25 h / 0 °C

8: 100 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

9: 93 percent / NaH; n-Bu₄NI / dimethylformamide; tetrahydrofuran / 24 h / 20 °C

10: 92 percent / LDA / tetrahydrofuran; hexane / 2 h / 0 °C

11: 100 percent / PPTS / methanol / 24 h / 20 °C

With disodium hydrogenphosphate; copper(l) iodide; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; propynoic acid ethyl ester; lithium diisopropyl amide; diethylazodicarboxylate; In tetrahydrofuran; pyridine; methanol; diethyl ether; hexane; chloroform; N,N-dimethyl-formamide; toluene; benzene; 5: Mitsunobu reaction / 6: intramolecular Diels-Alder reaction;
DOI:10.1021/jo0015772

Reference yield:

: 331627-32-8
6-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-6-methyl-cyclohex-2-enone

: 331627-42-0
(2aS,3R,6R,8aR,8bS)-2a,3,4,6,7,8,8a,8b-octahydro-6-benzyloxymethyl-[1,8-bc]-3,6-dimethylnaphtho-2-furanone

Guidance literature:: Multi-step reaction with 9 steps

1: 21.6 g / tetrahydrofuran / 6 h / 0 °C

2: 93 percent / Et₃N / benzene / 1 h / 20 °C

3: 8.75 g / DIBAL-H / toluene / 0.5 h / -78 °C

4: 97 percent / m-CPBA; Na₂HPO₄ / CHCl₃ / 0.5 h / -42 °C

5: 98 percent / DEAD; PPh₃ / tetrahydrofuran / 1 h / 20 °C

6: 89 percent / ethyl propiolate / pyridine; toluene / 8 h / Heating

7: 88 percent / CuI / diethyl ether / 0.25 h / 0 °C

8: 100 percent / TBAF / tetrahydrofuran / 1 h / 20 °C

9: 93 percent / NaH; n-Bu₄NI / dimethylformamide; tetrahydrofuran / 24 h / 20 °C

With disodium hydrogenphosphate; copper(l) iodide; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; propynoic acid ethyl ester; diethylazodicarboxylate; In tetrahydrofuran; pyridine; diethyl ether; chloroform; N,N-dimethyl-formamide; toluene; benzene; 5: Mitsunobu reaction / 6: intramolecular Diels-Alder reaction;
DOI:10.1021/jo0015772