(S,E)-6-tert-butyldiphenylsilyloxy-4-methyl-1-((1S,3R,5S)-5-methyl-1-((2R,5R,)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)-2-methylenehex-4-en-1-ol

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Chemical Name:(S,E)-6-tert-butyldiphenylsilyloxy-4-methyl-1-((1S,3R,5S)-5-methyl-1-((2R,5R,)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)-2-methylenehex-4-en-1-ol
CAS No.:1404459-35-3
Molecular Formula:C₃₈H₅₂O₅Si
Molecular Weight:616.913
Hs Code.:

(S,E)-6-tert-butyldiphenylsilyloxy-4-methyl-1-((1S,3R,5S)-5-methyl-1-((2R,5R,)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)-2-methylenehex-4-en-1-ol

Synonyms:(S,E)-6-tert-butyldiphenylsilyloxy-4-methyl-1-((1S,3R,5S)-5-methyl-1-((2R,5R,)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)-2-methylenehex-4-en-1-ol

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Chemical Property of (S,E)-6-tert-butyldiphenylsilyloxy-4-methyl-1-((1S,3R,5S)-5-methyl-1-((2R,5R,)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)-2-methylenehex-4-en-1-ol

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Technology Process of (S,E)-6-tert-butyldiphenylsilyloxy-4-methyl-1-((1S,3R,5S)-5-methyl-1-((2R,5R,)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)-2-methylenehex-4-en-1-ol

There total 7 articles about (S,E)-6-tert-butyldiphenylsilyloxy-4-methyl-1-((1S,3R,5S)-5-methyl-1-((2R,5R,)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)-2-methylenehex-4-en-1-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: 82.0%

: 1291069-95-8
(1S,3R,5S)-5-methyl-1-((2R,5R)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octane-3-carboxaldehyde

: 1404458-69-0
(E)-tert-butyl((5-iodo-3-methylhexa-2,5-diendien-1-yl)oxy)diphenylsilane

: 1404459-35-3
(S,E)-6-tert-butyldiphenylsilyloxy-4-methyl-1-((1S,3R,5S)-5-methyl-1-((2R,5R,)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)-2-methylenehex-4-en-1-ol

Guidance literature:: With chromium dichloride; manganese; zirconocene dichloride; N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; C₁₀H₁₀O₄*NiCl₂; lithium chloride; In acetonitrile; at 20 ℃; for 2h; stereoselective reaction; Inert atmosphere;
DOI:10.1021/ol302751b

Reference yield:

: (E)-tert-butyl((5-iodo-3-methylhexa-2,5-diendien-1-yl)oxy)diphenylsilane

: 1404459-35-3
(S,E)-6-tert-butyldiphenylsilyloxy-4-methyl-1-((1S,3R,5S)-5-methyl-1-((2R,5R,)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)-2-methylenehex-4-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: N-iodo-succinimide / dichloromethane / 0.17 h / 0 °C

2: N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; chromium dichloride; lithium chloride; manganese; C₁₀H₁₀O₄*NiCl₂; zirconocene dichloride / acetonitrile / 2 h / 20 °C / Inert atmosphere

With chromium dichloride; manganese; N-iodo-succinimide; zirconocene dichloride; N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; C₁₀H₁₀O₄*NiCl₂; lithium chloride; In dichloromethane; acetonitrile; 2: |Nozaki-Hiyama-Kishi Reaction;
DOI:10.1021/ol302751b

Reference yield:

: (E)-3-methylhex-2-en-5-yn-1-ol

: 1404459-35-3
(S,E)-6-tert-butyldiphenylsilyloxy-4-methyl-1-((1S,3R,5S)-5-methyl-1-((2R,5R,)-5-methyl-5-vinyltetrahydrofuran-2-yl)-2,8-dioxabicyclo[3.2.1]octan-3-yl)-2-methylenehex-4-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 1H-imidazole / dichloromethane / 2 h / 0 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -40 °C / Inert atmosphere

2.2: 2.5 h / -78 °C / Inert atmosphere

3.1: N-iodo-succinimide / dichloromethane / 0.17 h / 0 °C

4.1: N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; chromium dichloride; lithium chloride; manganese; C₁₀H₁₀O₄*NiCl₂; zirconocene dichloride / acetonitrile / 2 h / 20 °C / Inert atmosphere

With 1H-imidazole; chromium dichloride; manganese; N-iodo-succinimide; n-butyllithium; zirconocene dichloride; N-(2-((S)-4-isopropyl-4,5-dihydrooxazol-2-yl)-6-(((1S,2R,5S)-2-isopropyl-5-methylcyclohexyl)oxy)phenyl)benzenesulfonamide; C₁₀H₁₀O₄*NiCl₂; lithium chloride; In tetrahydrofuran; hexane; dichloromethane; acetonitrile; 4.1: |Nozaki-Hiyama-Kishi Reaction;
DOI:10.1021/ol302751b