[(1S,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methoxy(1,1-dimethylethyl)dimethylsilane

Base Information

Chemical Name:[(1S,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methoxy(1,1-dimethylethyl)dimethylsilane
CAS No.:935264-69-0
Molecular Formula:C₂₈H₅₀O₄Si₂
Molecular Weight:506.874
Hs Code.:

[(1S,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methoxy(1,1-dimethylethyl)dimethylsilane

Synonyms:[(1S,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methoxy(1,1-dimethylethyl)dimethylsilane

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Chemical Property of [(1S,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methoxy(1,1-dimethylethyl)dimethylsilane

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Technology Process of [(1S,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methoxy(1,1-dimethylethyl)dimethylsilane

There total 11 articles about [(1S,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methoxy(1,1-dimethylethyl)dimethylsilane 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: 88.0%

: 935264-68-9
(1S,5R,6R)-6-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-ol

: 18162-48-6
tert-butyldimethylsilyl chloride

: 935264-69-0
[(1S,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methoxy(1,1-dimethylethyl)dimethylsilane

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 96h;
DOI:10.1021/jo061456n

Reference yield:

: 176774-93-9
(5S,6S)-6-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one

: 935264-69-0
[(1S,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methoxy(1,1-dimethylethyl)dimethylsilane

Guidance literature:: Multi-step reaction with 9 steps

1: 89 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 2.5 h / 0 - 20 °C

2: 80 percent / TBHP; VO(acac)2 / benzene; toluene / 2 h / 20 °C

3: NaH / dimethylformamide / 10 h / 20 °C

4: 4-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; H₂O / 16 h / 20 °C

5: 17.02 g / NaIO₄ / tetrahydrofuran; H₂O / 0.25 h / 20 °C

6: 76 percent / m-CPBA / hexane; ethyl acetate / 72 h / 20 °C

7: 86 percent / AcOH; NaOAc; NaI / Zn / CH₂Cl₂ / 48 h / Heating

8: 97 percent / K₂CO₃ / methanol / 2 h / 20 °C

9: 88 percent / imiazole / dimethylformamide / 96 h / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; cerium(III) chloride; bis(acetylacetonate)oxovanadium; sodium acetate; sodium hydride; potassium carbonate; acetic acid; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; sodium iodide; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 6: Baeyer-Villiger rearrangement;
DOI:10.1021/jo061456n

Reference yield:

: 935264-61-2
(1R,5S,6S)-6-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol

: 935264-69-0
[(1S,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methoxy(1,1-dimethylethyl)dimethylsilane

Guidance literature:: Multi-step reaction with 8 steps

1: 80 percent / TBHP; VO(acac)2 / benzene; toluene / 2 h / 20 °C

2: NaH / dimethylformamide / 10 h / 20 °C

3: 4-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; H₂O / 16 h / 20 °C

4: 17.02 g / NaIO₄ / tetrahydrofuran; H₂O / 0.25 h / 20 °C

5: 76 percent / m-CPBA / hexane; ethyl acetate / 72 h / 20 °C

6: 86 percent / AcOH; NaOAc; NaI / Zn / CH₂Cl₂ / 48 h / Heating

7: 97 percent / K₂CO₃ / methanol / 2 h / 20 °C

8: 88 percent / imiazole / dimethylformamide / 96 h / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; bis(acetylacetonate)oxovanadium; sodium acetate; sodium hydride; potassium carbonate; acetic acid; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; sodium iodide; zinc; In tetrahydrofuran; methanol; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene; benzene; 5: Baeyer-Villiger rearrangement;
DOI:10.1021/jo061456n