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

Base Information

Chemical Name:(1R,5S,6S)-6-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-ol
CAS No.:935265-09-1
Molecular Formula:C₂₂H₃₆O₄Si
Molecular Weight:392.611
Hs Code.:

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

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Chemical Property of (1R,5S,6S)-6-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-ol

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Technology Process of (1R,5S,6S)-6-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-ol

There total 10 articles about (1R,5S,6S)-6-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-ol 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: 90.0%

: 935265-07-9
(1R,5S,6S)-6-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yl acetate

: 935265-09-1
(1R,5S,6S)-6-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-ol

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 2h;
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

: 935265-09-1
(1R,5S,6S)-6-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-ol

Guidance literature:: Multi-step reaction with 7 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

With 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

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

: 935265-09-1
(1R,5S,6S)-6-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-ol

Guidance literature:: Multi-step reaction with 6 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

With sodium periodate; osmium(VIII) oxide; 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; 4: Baeyer-Villiger rearrangement;
DOI:10.1021/jo061456n