(6S,7E,9R,10S,11E)-9-isopropyl-7-[(R)-N-methyl-S-phenylsulfonimidoyl]-10-(triethylsilyloxy)trideca-1,7,11-trien-6-ol

Base Information

Chemical Name:(6S,7E,9R,10S,11E)-9-isopropyl-7-[(R)-N-methyl-S-phenylsulfonimidoyl]-10-(triethylsilyloxy)trideca-1,7,11-trien-6-ol
CAS No.:1380215-76-8
Molecular Formula:C₂₉H₄₉NO₃SSi
Molecular Weight:519.864
Hs Code.:

Synonyms:(6S,7E,9R,10S,11E)-9-isopropyl-7-[(R)-N-methyl-S-phenylsulfonimidoyl]-10-(triethylsilyloxy)trideca-1,7,11-trien-6-ol

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Chemical Property of (6S,7E,9R,10S,11E)-9-isopropyl-7-[(R)-N-methyl-S-phenylsulfonimidoyl]-10-(triethylsilyloxy)trideca-1,7,11-trien-6-ol

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Technology Process of (6S,7E,9R,10S,11E)-9-isopropyl-7-[(R)-N-methyl-S-phenylsulfonimidoyl]-10-(triethylsilyloxy)trideca-1,7,11-trien-6-ol

There total 4 articles about (6S,7E,9R,10S,11E)-9-isopropyl-7-[(R)-N-methyl-S-phenylsulfonimidoyl]-10-(triethylsilyloxy)trideca-1,7,11-trien-6-ol 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: 94.0%

: 1380215-68-8
(2E,4R,5S,6E)-4-isopropyl-2-[(R)-N-methyl-S-phenylsulfonimidoyl]-5-(triethylsilyloxy)octa-2,6-dienal

: 34164-50-6
4-penten-1-ylmagnesium bromide

: 1380215-76-8
(6S,7E,9R,10S,11E)-9-isopropyl-7-[(R)-N-methyl-S-phenylsulfonimidoyl]-10-(triethylsilyloxy)trideca-1,7,11-trien-6-ol

Guidance literature:: In tetrahydrofuran; at -78 ℃; for 1h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/chem.201103060

Reference yield:

: 918637-15-7
(1Z,3R,4S,5E)-3-isopropyl-1-[(S)-N-methyl-S-phenyl-sulfonimidoyl]-hepta-1,5-dien-4-ol

: 1380215-76-8
(6S,7E,9R,10S,11E)-9-isopropyl-7-[(R)-N-methyl-S-phenylsulfonimidoyl]-10-(triethylsilyloxy)trideca-1,7,11-trien-6-ol

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 / 0 °C / Inert atmosphere

3.1: tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; In tetrahydrofuran; hexane; N,N-dimethyl-formamide;
DOI:10.1002/chem.201103060

Reference yield:

: 918637-17-9
triethyl((1Z,3R,4S,5E)-3-isopropyl-1-[(S)-N-methyl-S-phenylsulfonimidoyl]hepta-1,5-dien-4-yloxy)silane

: 1380215-76-8
(6S,7E,9R,10S,11E)-9-isopropyl-7-[(R)-N-methyl-S-phenylsulfonimidoyl]-10-(triethylsilyloxy)trideca-1,7,11-trien-6-ol

Guidance literature:: Multi-step reaction with 2 steps

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

1.2: 2 h / 0 °C / Inert atmosphere

2.1: tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

With n-butyllithium; In tetrahydrofuran; hexane;
DOI:10.1002/chem.201103060