(5S,6E,8R,9S)-5,9-di(but-3-enyl)-11,11-diethyl-8-isopropyl-2,2,3,3-tetramethyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-4,10-dioxa-3,11-disilatridec-6-ene

Base Information

• Chemical Name: (5S,6E,8R,9S)-5,9-di(but-3-enyl)-11,11-diethyl-8-isopropyl-2,2,3,3-tetramethyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-4,10-dioxa-3,11-disilatridec-6-ene
• CAS No.: 918637-30-6
• Molecular Formula: C₃₅H₆₃NO₃SSi₂
• Molecular Weight: 634.127

Synonyms:(5S,6E,8R,9S)-5,9-di(but-3-enyl)-11,11-diethyl-8-isopropyl-2,2,3,3-tetramethyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-4,10-dioxa-3,11-disilatridec-6-ene

Chemical Property of (5S,6E,8R,9S)-5,9-di(but-3-enyl)-11,11-diethyl-8-isopropyl-2,2,3,3-tetramethyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-4,10-dioxa-3,11-disilatridec-6-ene

Chemical Property:

Purity/Quality:

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Technology Process of (5S,6E,8R,9S)-5,9-di(but-3-enyl)-11,11-diethyl-8-isopropyl-2,2,3,3-tetramethyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-4,10-dioxa-3,11-disilatridec-6-ene

There total 5 articles about (5S,6E,8R,9S)-5,9-di(but-3-enyl)-11,11-diethyl-8-isopropyl-2,2,3,3-tetramethyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-4,10-dioxa-3,11-disilatridec-6-ene 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%

(5S,6E,8R,9S)-8-isopropyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-9-(triethylsilyloxy)trideca-1,6,12-trien-5-ol (918637-26-0) + tert-butyldimethylsilyl chloride (18162-48-6) → (5S,6E,8R,9S)-5,9-di(but-3-enyl)-11,11-diethyl-8-isopropyl-2,2,3,3-tetramethyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-4,10-dioxa-3,11-disilatridec-6-ene (918637-30-6)

Guidance literature:

(5S,6E,8R,9S)-8-isopropyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-9-(triethylsilyloxy)trideca-1,6,12-trien-5-ol; With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 1h; Inert atmosphere;

tert-butyldimethylsilyl chloride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 20h; Inert atmosphere;

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) → (5S,6E,8R,9S)-5,9-di(but-3-enyl)-11,11-diethyl-8-isopropyl-2,2,3,3-tetramethyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-4,10-dioxa-3,11-disilatridec-6-ene (918637-30-6)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;

DOI:10.1002/chem.201103060

Reference yield:

triethyl((3R,4S,Z)-3-isopropyl-1-[(S)-N-methyl-S-phenylsulfonimidoyl]octa-1,7-dien-4-yloxy)triethylsilane (918637-18-0) → (5S,6E,8R,9S)-5,9-di(but-3-enyl)-11,11-diethyl-8-isopropyl-2,2,3,3-tetramethyl-6-[(R)-N-methyl-S-phenylsulfonimidoyl]-4,10-dioxa-3,11-disilatridec-6-ene (918637-30-6)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 2 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

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; hexane; 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

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

tert-butyldimethylsilyl chloride

Downstream raw materials:

((1S,2R,3E,5S,8E,12S,13R,14E,16S,19E)-5,16-bis(tert-butyldimethylsilyloxy)-2,13-diisopropyl-4,15-bis[(R)-N-methyl-S-phenylsulfonimidoyl]cyclodocosa-3,8,14,19-tetraene-1,12-diyl)bis(oxy)bis(triethylsilane)

((1S,4E,8S,9R,10E,12S,15E,19S,20E,22R)-12,19-bis(tert-butyldimethylsilyloxy)-9,22-diisopropyl-11,20-bis-[(R)-N-methyl-S-phenyl-sulfonimidoyl]cyclodocosa-4,10,-15,20-tetraene-1,8-diyl)bis(oxy)bis-(triethylsilane)

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