(2E,4R,5S,8Z)-4-isopropyl-2-[(R)-N-methyl-S-phenylsulfonimidoyl]-5-(triethylsilyl-oxy)cycloundeca-2,8-dienone

Base Information

• Chemical Name: (2E,4R,5S,8Z)-4-isopropyl-2-[(R)-N-methyl-S-phenylsulfonimidoyl]-5-(triethylsilyl-oxy)cycloundeca-2,8-dienone
• CAS No.: 918637-42-0
• Molecular Formula: C₂₇H₄₃NO₃SSi
• Molecular Weight: 489.795

Synonyms:(2E,4R,5S,8Z)-4-isopropyl-2-[(R)-N-methyl-S-phenylsulfonimidoyl]-5-(triethylsilyl-oxy)cycloundeca-2,8-dienone

Chemical Property of (2E,4R,5S,8Z)-4-isopropyl-2-[(R)-N-methyl-S-phenylsulfonimidoyl]-5-(triethylsilyl-oxy)cycloundeca-2,8-dienone

Chemical Property:

Purity/Quality:

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Technology Process of (2E,4R,5S,8Z)-4-isopropyl-2-[(R)-N-methyl-S-phenylsulfonimidoyl]-5-(triethylsilyl-oxy)cycloundeca-2,8-dienone

There total 8 articles about (2E,4R,5S,8Z)-4-isopropyl-2-[(R)-N-methyl-S-phenylsulfonimidoyl]-5-(triethylsilyl-oxy)cycloundeca-2,8-dienone 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: 96.0%

(1R,2E,4R,5S,8Z)-4-isopropyl-2-[(R)-N-methyl-S-phenylsulfonimidoyl]-5-(triethyl-silyloxy)cycloundeca-2,8-dienol (918637-41-9) → (2E,4R,5S,8Z)-4-isopropyl-2-[(R)-N-methyl-S-phenylsulfonimidoyl]-5-(triethylsilyl-oxy)cycloundeca-2,8-dienone (918637-42-0)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1002/chem.201103060

Reference yield:

(+)-(E,S)-4-methyl-1-(N-methyl-S-phenylsulfonimidoyl)-pent-2-ene (172748-29-7) → (2E,4R,5S,8Z)-4-isopropyl-2-[(R)-N-methyl-S-phenylsulfonimidoyl]-5-(triethylsilyl-oxy)cycloundeca-2,8-dienone (918637-42-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 - 20 °C / Inert atmosphere

1.3: 2.75 h / -78 °C / Inert atmosphere

2.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

2.2: 20 h / 0 - 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C / Inert atmosphere

3.2: 2 h / -78 °C / Inert atmosphere

4.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

4.2: 20 h / 0 - 20 °C / Inert atmosphere

5.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 16 h / Inert atmosphere; Reflux

6.1: acetic acid / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere

7.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; n-butyllithium; Dess-Martin periodane; acetic acid; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/chem.201103060

Reference yield:

(3R,4S,Z)-3-isopropyl-1-[(S)-N-methyl-S-phenylsulfonimidoyl]octa-1,7-dien-4-ol (918637-16-8) → (2E,4R,5S,8Z)-4-isopropyl-2-[(R)-N-methyl-S-phenylsulfonimidoyl]-5-(triethylsilyl-oxy)cycloundeca-2,8-dienone (918637-42-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

1.2: 20 h / 0 - 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / -78 - 0 °C / Inert atmosphere

2.2: 2 h / -78 °C / Inert atmosphere

3.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

3.2: 20 h / 0 - 20 °C / Inert atmosphere

4.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 16 h / Inert atmosphere; Reflux

5.1: acetic acid / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere

6.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; n-butyllithium; Dess-Martin periodane; acetic acid; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1002/chem.201103060

upstream raw materials:

(3R,4S,Z)-3-isopropyl-1-[(S)-N-methyl-S-phenylsulfonimidoyl]octa-1,7-dien-4-ol

triethyl((3R,4S,Z)-3-isopropyl-1-[(S)-N-methyl-S-phenylsulfonimidoyl]octa-1,7-dien-4-yloxy)triethylsilane

tert-butyl((1R,2E,4R,5S,8Z)-4-isopropyl-2-[(R)-N-methyl-S-phenylsulfonimidoyl]-5-(triethylsilyloxy)cycloundeca-2,8-dienyloxy)dimethylsilane

(1R,2E,4R,5S,8Z)-4-isopropyl-2-[(R)-N-methyl-S-phenylsulfonimidoyl]-5-(triethyl-silyloxy)cycloundeca-2,8-dienol

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