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

Base Information

Chemical Name:[(1R,2S,6R)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methanol
CAS No.:935265-12-6
Molecular Formula:C₂₂H₃₆O₄Si
Molecular Weight:392.611
Hs Code.:

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

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

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

There total 12 articles about [(1R,2S,6R)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methanol 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: 29.0%

: 935265-10-4
[(1R,2S,6R)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methoxy(1,1-dimethylethyl)dimethylsilane

: 935265-12-6
[(1R,2S,6R)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methanol

Guidance literature:: With tetra(n-butyl)ammonium hydrogensulfate; toluene-4-sulfonic acid; In methanol; at -20 ℃; for 24h;
DOI:10.1021/jo061456n

Reference yield:

: 935265-01-3
(1S,5R,6R)-6-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol

: 935265-12-6
[(1R,2S,6R)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methanol

Guidance literature:: Multi-step reaction with 9 steps

1: 78 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: 18.06 g / NaIO₄ / tetrahydrofuran; H₂O / 0.25 h / 20 °C

5: 73 percent / m-CPBA / hexane; ethyl acetate / 72 h / 20 °C

6: 88 percent / AcOH; NaOAc; NaI / Zn / CH₂Cl₂ / 48 h / Heating

7: 90 percent / K₂CO₃ / methanol / 2 h / 20 °C

8: 83 percent / imiazole / dimethylformamide / 96 h / 20 °C

9: 29 percent / nBu₄NHSO₄; p-TsOH*H₂O / methanol / 24 h / -20 °C

With 1H-imidazole; tert.-butylhydroperoxide; sodium periodate; osmium(VIII) oxide; bis(acetylacetonate)oxovanadium; sodium acetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 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

Reference yield:

: 935264-92-9
(1S,2S,3R,4R,6R)-3-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-1-methyl-4-(1-methylethenyl)-7-oxabicyclo[4.1.0]heptan-2-ol

: 935265-12-6
[(1R,2S,6R)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]methanol

Guidance literature:: Multi-step reaction with 8 steps

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

2: 4-methylmorpholine-N-oxide; OsO₄ / tetrahydrofuran; H₂O / 16 h / 20 °C

3: 18.06 g / NaIO₄ / tetrahydrofuran; H₂O / 0.25 h / 20 °C

4: 73 percent / m-CPBA / hexane; ethyl acetate / 72 h / 20 °C

5: 88 percent / AcOH; NaOAc; NaI / Zn / CH₂Cl₂ / 48 h / Heating

6: 90 percent / K₂CO₃ / methanol / 2 h / 20 °C

7: 83 percent / imiazole / dimethylformamide / 96 h / 20 °C

8: 29 percent / nBu₄NHSO₄; p-TsOH*H₂O / methanol / 24 h / -20 °C

With 1H-imidazole; sodium periodate; osmium(VIII) oxide; sodium acetate; tetra(n-butyl)ammonium hydrogensulfate; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; 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; 4: Baeyer-Villiger rearrangement;
DOI:10.1021/jo061456n