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

Base Information

• Chemical Name: (1S,5R,6R)-6-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yl acetate
• CAS No.: 935264-67-8
• Molecular Formula: C₂₄H₃₈O₅Si
• Molecular Weight: 434.648

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

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

Chemical Property:

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

There total 9 articles about (1S,5R,6R)-6-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yl acetate 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: 86.0%

(1S,3S,4R,5R,6S)-4-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-5-(4-methoxybenzyloxy)-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl acetate (935264-66-7) → (1S,5R,6R)-6-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yl acetate (935264-67-8)

Guidance literature:

With sodium acetate; acetic acid; sodium iodide; zinc; In dichloromethane; for 48h; Heating;

DOI:10.1021/jo061456n

Reference yield:

(5S,6S)-6-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one (176774-93-9) → (1S,5R,6R)-6-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yl acetate (935264-67-8)

Guidance literature:

Multi-step reaction with 7 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

With tert.-butylhydroperoxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; cerium(III) chloride; bis(acetylacetonate)oxovanadium; sodium acetate; sodium hydride; 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:

(1R,5S,6S)-6-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol (935264-61-2) → (1S,5R,6R)-6-(1,1-dimethylethyl)dimethylsilyloxymethyl-5-(4-methoxybenzyloxy)-4-methylcyclohex-3-en-1-yl acetate (935264-67-8)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1021/jo061456n

upstream raw materials:

(1S,3S,4R,5R,6S)-4-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-5-(4-methoxybenzyloxy)-6-methyl-7-oxabicyclo[4.1.0]heptan-3-yl acetate

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

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

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

Downstream raw materials:

(4E,7S)-N-{(2R)-[(1R,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]-2-methoxyethyl}-7-methoxydodec-4-enamide

(4E,7S)-N-{(2S)-[(1R,2R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-2-(4-methoxybenzyloxy)-3-methylcyclohex-3-en-1-yl]-2-methoxyethyl}-7-methoxydodec-4-enamide

(4E,7S)-N-{(2R)-[(1R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-3-methyl-2-oxocyclohex-3-en-1-yl]-2-methoxyethyl}-7-methoxydodec-4-enamide

(4E,7S)-N-{(2S)-[(1R,6S)-6-(1,1-dimethylethyl)dimethylsilyloxy-3-methyl-2-oxocyclohex-3-en-1-yl]-2-methoxyethyl}-7-methoxydodec-4-enamide

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