(E,8R,9S)-8-isopropyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-9-(triethylsilyloxy)trideca-1,6,12-trien-5-one

Base Information

• Chemical Name: (E,8R,9S)-8-isopropyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-9-(triethylsilyloxy)trideca-1,6,12-trien-5-one
• CAS No.: 1380215-81-5
• Molecular Formula: C₂₉H₄₇NO₃SSi
• Molecular Weight: 517.849

Synonyms:(E,8R,9S)-8-isopropyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-9-(triethylsilyloxy)trideca-1,6,12-trien-5-one

Chemical Property of (E,8R,9S)-8-isopropyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-9-(triethylsilyloxy)trideca-1,6,12-trien-5-one

Chemical Property:

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Technology Process of (E,8R,9S)-8-isopropyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-9-(triethylsilyloxy)trideca-1,6,12-trien-5-one

There total 3 articles about (E,8R,9S)-8-isopropyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-9-(triethylsilyloxy)trideca-1,6,12-trien-5-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: 96.0%

(6E,8R,9S)-8-isopropyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-9-(triethylsilyloxy)trideca-1,6,12-trien-5-ol → (E,8R,9S)-8-isopropyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-9-(triethylsilyloxy)trideca-1,6,12-trien-5-one (1380215-81-5)

Guidance literature:

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

DOI:10.1002/chem.201103060

Reference yield:

4-pentenal (2100-17-6) → (E,8R,9S)-8-isopropyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-9-(triethylsilyloxy)trideca-1,6,12-trien-5-one (1380215-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 3 h / -78 - 0 °C / Inert atmosphere; Schlenk technique

1.2: 2 h / -78 °C / Inert atmosphere; Schlenk technique

2.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Schlenk technique

With n-butyllithium; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1002/ejoc.201301461

Reference yield:

triethyl((3R,4S,Z)-3-isopropyl-1-[(S)-N-methyl-S-phenylsulfonimidoyl]octa-1,7-dien-4-yloxy)triethylsilane (918637-18-0) → (E,8R,9S)-8-isopropyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-9-(triethylsilyloxy)trideca-1,6,12-trien-5-one (1380215-81-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 3 h / -78 - 0 °C / Inert atmosphere; Schlenk technique

1.2: 2 h / -78 °C / Inert atmosphere; Schlenk technique

2.1: Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C / Inert atmosphere; Schlenk technique

With n-butyllithium; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1002/ejoc.201301461

upstream raw materials:

4-pentenal

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

Downstream raw materials:

(2R,5R,6S)-2,6-di(but-3-enyl)-5-isopropyl-3-[(S)-N-methyl-S-phenylsulfonimidoyl]-5,6-dihydro-2H-pyran-2-ol

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