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

Base Information

• Chemical Name: (5S,6S)-6-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one
• CAS No.: 176774-93-9
• Molecular Formula: C₁₇H₃₀O₂Si
• Molecular Weight: 294.51

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

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

Chemical Property:

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

There total 2 articles about (5S,6S)-6-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one 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%

tert-butyldimethylsilyl chloride (18162-48-6) + (5S,6S)-6-(hydroxymethyl)-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one (176774-92-8) → (5S,6S)-6-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one (176774-93-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 10h;

DOI:10.1021/jo061456n

Reference yield:

(S)-p-mentha-6,8-dien-2-one (2244-16-8,6485-40-1) → (5S,6S)-6-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one (176774-93-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 59 percent / LDA / tetrahydrofuran / -84 - 20 °C

2: 94 percent / imidazole / dimethylformamide / 10 h / 20 °C

With 1H-imidazole; lithium diisopropyl amide; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo061456n

Reference yield: 89.0%

(5S,6S)-6-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one (176774-93-9) → (1R,5S,6S)-6-[(1,1-dimethylethyl)dimethylsilyloxymethyl]-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-ol (935264-61-2)

Guidance literature:

With sodium tetrahydroborate; cerium(III) chloride; In methanol; at 0 - 20 ℃; for 2.5h;

DOI:10.1021/jo061456n

upstream raw materials:

tert-butyldimethylsilyl chloride

(5S,6S)-6-(hydroxymethyl)-2-methyl-5-(1-methylethenyl)-2-cyclohexen-1-one

(S)-p-mentha-6,8-dien-2-one

Downstream raw materials:

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

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

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

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

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