(4R,5S)-4-tert-butyldimethylsilyloxy-5-(4-methoxyphenyl)cyclohex-2-en-1-one

Base Information

• Chemical Name: (4R,5S)-4-tert-butyldimethylsilyloxy-5-(4-methoxyphenyl)cyclohex-2-en-1-one
• CAS No.: 289503-61-3
• Molecular Formula: C₁₉H₂₈O₃Si
• Molecular Weight: 332.515

Synonyms:(4R,5S)-4-tert-butyldimethylsilyloxy-5-(4-methoxyphenyl)cyclohex-2-en-1-one

Chemical Property of (4R,5S)-4-tert-butyldimethylsilyloxy-5-(4-methoxyphenyl)cyclohex-2-en-1-one

Chemical Property:

Purity/Quality:

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Technology Process of (4R,5S)-4-tert-butyldimethylsilyloxy-5-(4-methoxyphenyl)cyclohex-2-en-1-one

There total 4 articles about (4R,5S)-4-tert-butyldimethylsilyloxy-5-(4-methoxyphenyl)cyclohex-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%

tert-butyldimethylsilyl chloride (18162-48-6) + (1S,6R)-6-hydroxy-4'-methoxy-1,6-dihydro-[1,1'-biphenyl]-3(2H)-one (289503-60-2) → (4R,5S)-4-tert-butyldimethylsilyloxy-5-(4-methoxyphenyl)cyclohex-2-en-1-one (289503-61-3)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 20 ℃; for 24h;

DOI:10.3987/COM-00-8907

Reference yield:

(4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one (121651-99-8) → (4R,5S)-4-tert-butyldimethylsilyloxy-5-(4-methoxyphenyl)cyclohex-2-en-1-one (289503-61-3)

Guidance literature:

Multi-step reaction with 2 steps

1: CuCN / diethyl ether / 0.5 h / -20 °C

2: 70 percent / imidazole / CH₂Cl₂ / 24 h / 20 °C

With 1H-imidazole; In diethyl ether; dichloromethane; 1: Grignard reaction / 2: Etherification;

DOI:10.3987/COM-00-8907

Reference yield:

4-methoxyphenyl magnesium bromide (13139-86-1) → (4R,5S)-4-tert-butyldimethylsilyloxy-5-(4-methoxyphenyl)cyclohex-2-en-1-one (289503-61-3)

Guidance literature:

Multi-step reaction with 2 steps

1: CuCN / diethyl ether / 0.5 h / -20 °C

2: 70 percent / imidazole / CH₂Cl₂ / 24 h / 20 °C

With 1H-imidazole; In diethyl ether; dichloromethane; 1: Grignard reaction / 2: Etherification;

DOI:10.3987/COM-00-8907

upstream raw materials:

tert-butyldimethylsilyl chloride

(1S,6R)-6-hydroxy-4'-methoxy-1,6-dihydro-[1,1'-biphenyl]-3(2H)-one

(4S,5R)-4,5-O-isopropylidenedioxycyclohex-2-en-1-one

4-methoxyphenyl magnesium bromide

Downstream raw materials:

(4R,5S)-4-tert-butyldimethylsilyloxy-1-hydroxy-1,5-bis(4-methoxyphenyl)cyclohex-2-en-1-ol

(4S,5S)-4-tert-butyldimethylsilyloxy-1,2,3-trihydroxy-1,5-bis(4-methoxyphenyl)cyclohexane

(S)-3-(S)-1,4-Dioxa-spiro[4.5]dec-2-yl-1,3-bis-(4-methoxy-phenyl)-propan-1-ol

(3S,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-1,3-bis-(4-methoxy-phenyl)-pentane-1,5-diol

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