(1'S,6S)-6-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-3-methylcyclohex-2-en-1-one

Base Information

• Chemical Name: (1'S,6S)-6-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-3-methylcyclohex-2-en-1-one
• CAS No.: 252289-24-0
• Molecular Formula: C₁₈H₃₄O₂Si
• Molecular Weight: 310.552

Synonyms:(1'S,6S)-6-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-3-methylcyclohex-2-en-1-one

Chemical Property of (1'S,6S)-6-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-3-methylcyclohex-2-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1'S,6S)-6-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-3-methylcyclohex-2-en-1-one

There total 6 articles about (1'S,6S)-6-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-3-methylcyclohex-2-en-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: 70.0%

(3R,6S)-2-Bromo-6-{(S)-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-1-methyl-ethyl}-3-methyl-cyclohexanone (252289-23-9) → (1'S,6S)-6-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-3-methylcyclohex-2-en-1-one (252289-24-0)

Guidance literature:

In 2,4,6-trimethyl-pyridine; at 145 - 150 ℃; for 1h;

DOI:10.1002/(SICI)1522-2675(19991006)82:10<1610::AID-HLCA1610>3.0.CO;2-T

Reference yield:

chlorodimethyl(1,1,2-trimethylpropyl)silane (67373-56-2) → (1'S,6S)-6-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-3-methylcyclohex-2-en-1-one (252289-24-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / 1H-imidazole / dimethylformamide / 15 h / 0 - 20 °C

2: 65 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -78 °C

3: 100 percent / BuLi; (i-Pr)2NH / hexane; tetrahydrofuran / 1 h / -78 °C

4: N-bromosuccinimide / tetrahydrofuran / 2 h / 0 °C

5: 70 percent / 2,4,6-trimethyl-pyridine / 1 h / 145 - 150 °C

With 1H-imidazole; N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; diisopropylamine; In tetrahydrofuran; 2,4,6-trimethyl-pyridine; hexane; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Oxidation / 3: Etherification / 4: Bromination / 5: Dehydrobromination;

DOI:10.1002/(SICI)1522-2675(19991006)82:10<1610::AID-HLCA1610>3.0.CO;2-T

Reference yield:

(1R,2S,5R)-2-[(S)-2-hydroxy-1-methylethyl]-5-methylcyclohexan-1-ol (13834-16-7) → (1'S,6S)-6-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-3-methylcyclohex-2-en-1-one (252289-24-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 85 percent / 1H-imidazole / dimethylformamide / 15 h / 0 - 20 °C

2: 65 percent / (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 3 h / -78 °C

3: 100 percent / BuLi; (i-Pr)2NH / hexane; tetrahydrofuran / 1 h / -78 °C

4: N-bromosuccinimide / tetrahydrofuran / 2 h / 0 °C

5: 70 percent / 2,4,6-trimethyl-pyridine / 1 h / 145 - 150 °C

With 1H-imidazole; N-Bromosuccinimide; n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; diisopropylamine; In tetrahydrofuran; 2,4,6-trimethyl-pyridine; hexane; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Oxidation / 3: Etherification / 4: Bromination / 5: Dehydrobromination;

DOI:10.1002/(SICI)1522-2675(19991006)82:10<1610::AID-HLCA1610>3.0.CO;2-T

upstream raw materials:

(3R,6S)-2-Bromo-6-{(S)-2-[dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-1-methyl-ethyl}-3-methyl-cyclohexanone

chlorodimethyl(1,1,2-trimethylpropyl)silane

(1R,2S,5R)-2-[(S)-2-hydroxy-1-methylethyl]-5-methylcyclohexan-1-ol

(1'S,2S,5R)-2-{2'-{[dimethyl(1,1,2-trimethylpropyl)silyl]oxy}-1'-methylethyl}-5-methylcyclohexanone

Downstream raw materials:

(1'S,3R)-3-(4'-methylenecyclohex-2'-en-1'-yl)butanal

(1'R,2S)-2-(4'-methylenecyclohex-2'-en-1'-yl)propan-1-ol

(1'S,3R)-3-(4'-methylenecyclohex-2'-en-1'-yl)butanenitrile

(1'R,2S)-dimethyl{[2-(4'-methylenecyclohex-2'-en-1'-yl)propyl]oxy}(1,1,2-trimethylpropyl)silane

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