(2S,4R,5R,6E)-2-benzoyloxy-5-diethylisopropylsilyloxy-4-methyloct-6-en-3-one

Base Information

• Chemical Name: (2S,4R,5R,6E)-2-benzoyloxy-5-diethylisopropylsilyloxy-4-methyloct-6-en-3-one
• CAS No.: 1352831-83-4
• Molecular Formula: C₂₃H₃₆O₄Si
• Molecular Weight: 404.622

Synonyms:(2S,4R,5R,6E)-2-benzoyloxy-5-diethylisopropylsilyloxy-4-methyloct-6-en-3-one

Chemical Property of (2S,4R,5R,6E)-2-benzoyloxy-5-diethylisopropylsilyloxy-4-methyloct-6-en-3-one

Chemical Property:

Purity/Quality:

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Technology Process of (2S,4R,5R,6E)-2-benzoyloxy-5-diethylisopropylsilyloxy-4-methyloct-6-en-3-one

There total 5 articles about (2S,4R,5R,6E)-2-benzoyloxy-5-diethylisopropylsilyloxy-4-methyloct-6-en-3-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: 99.0%

chlorodiethylisopropylsilane (107149-56-4) + (2S,4R,5R,6E)-2-benzoyloxy-5-hydroxy-4-methyloct-6-en-3-one (173726-06-2) → (2S,4R,5R,6E)-2-benzoyloxy-5-diethylisopropylsilyloxy-4-methyloct-6-en-3-one (1352831-83-4)

Guidance literature:

With 1H-imidazole; In dichloromethane; at 0 - 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tet.2011.09.012

Reference yield:

(S)-2-hydroxypentan-(3)-one (125948-63-2) → (2S,4R,5R,6E)-2-benzoyloxy-5-diethylisopropylsilyloxy-4-methyloct-6-en-3-one (1352831-83-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; diethyl ether; dichloromethane / 14 h / 20 °C / Inert atmosphere

2.1: N,N-dimethyl-ethanamine / diethyl ether / 3 h / 0 °C / Inert atmosphere

3.1: diethyl ether / 16 h / -78 - -20 °C / Inert atmosphere

3.2: 1 h / 0 °C / pH 7 / aq. buffer

4.1: 1H-imidazole / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; N,N-dimethyl-ethanamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 3.1: Aldol reaction;

DOI:10.1016/j.tet.2011.09.012

Reference yield:

benzoic acid anhydride (93-97-0) → (2S,4R,5R,6E)-2-benzoyloxy-5-diethylisopropylsilyloxy-4-methyloct-6-en-3-one (1352831-83-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: dmap; N-ethyl-N,N-diisopropylamine / tetrahydrofuran; diethyl ether; dichloromethane / 14 h / 20 °C / Inert atmosphere

2.1: N,N-dimethyl-ethanamine / diethyl ether / 3 h / 0 °C / Inert atmosphere

3.1: diethyl ether / 16 h / -78 - -20 °C / Inert atmosphere

3.2: 1 h / 0 °C / pH 7 / aq. buffer

4.1: 1H-imidazole / dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; dmap; N,N-dimethyl-ethanamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 3.1: Aldol reaction;

DOI:10.1016/j.tet.2011.09.012

upstream raw materials:

(S)-2-hydroxypentan-⁽³⁾-one

chlorodiethylisopropylsilane

(2S,4R,5R,6E)-2-benzoyloxy-5-hydroxy-4-methyloct-6-en-3-one

benzoic acid anhydride

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