(S,E)-6-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)hex-5-en-1-ol

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Chemical Name:(S,E)-6-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)hex-5-en-1-ol
CAS No.:1586033-55-7
Molecular Formula:C₃₇H₅₈O₆Si
Molecular Weight:626.949
Hs Code.:

Synonyms:(S,E)-6-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)hex-5-en-1-ol

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Chemical Property of (S,E)-6-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)hex-5-en-1-ol

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Technology Process of (S,E)-6-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)hex-5-en-1-ol

There total 8 articles about (S,E)-6-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)hex-5-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: 90.0%

: 1586033-54-6
tert-butyl((R)-1-((4S,5S)-5-((S,E)-6-(4-methoxybenzyloxy)-3-(methoxymethoxy)hex-1-enyl)-2,2-dimethyl-1,3-dioxolan-4-yl)octyloxy)diphenylsilane

: 1586033-55-7
(S,E)-6-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)hex-5-en-1-ol

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 1h; Inert atmosphere;
DOI:10.1016/j.tet.2014.02.072

Reference yield:

: 1586033-59-1
C₉H₁₈O₂

: 1586033-55-7
(S,E)-6-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)hex-5-en-1-ol

Guidance literature:: Multi-step reaction with 8 steps

1.1: dmap; 1H-imidazole / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

2.2: 0 - 20 °C / Inert atmosphere

3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water / 12 h / 20 °C / Inert atmosphere

4.1: camphorsulphonic acid / dichloromethane / 20 °C / Inert atmosphere

5.1: diisobutylaluminium hydride / dichloromethane / 2.5 h / -78 °C / Inert atmosphere

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

6.2: 1 h / 20 °C / Inert atmosphere

7.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 24 h / Inert atmosphere; Reflux

8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 20 °C / Inert atmosphere

With 1H-imidazole; dmap; osmium(VIII) oxide; Hoveyda-Grubbs catalyst second generation; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; 2.1: |Horner-Wadsworth-Emmons Olefination / 2.2: |Horner-Wadsworth-Emmons Olefination / 6.1: |Wittig Olefination / 6.2: |Wittig Olefination / 7.1: |Cross Metathesis;
DOI:10.1016/j.tet.2014.02.072

Reference yield:

: 1586033-47-7
(R)-2-(tert-butyldiphenylsilyloxy)nonanal

: 1586033-55-7
(S,E)-6-((4S,5S)-5-((R)-1-(tert-butyldiphenylsilyloxy)octyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)hex-5-en-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

1.2: 0 - 20 °C / Inert atmosphere

2.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / tetrahydrofuran; water / 12 h / 20 °C / Inert atmosphere

3.1: camphorsulphonic acid / dichloromethane / 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / dichloromethane / 2.5 h / -78 °C / Inert atmosphere

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.25 h / 0 °C / Inert atmosphere

5.2: 1 h / 20 °C / Inert atmosphere

6.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 24 h / Inert atmosphere; Reflux

7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 20 °C / Inert atmosphere

With osmium(VIII) oxide; Hoveyda-Grubbs catalyst second generation; sodium hydride; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; 1.1: |Horner-Wadsworth-Emmons Olefination / 1.2: |Horner-Wadsworth-Emmons Olefination / 5.1: |Wittig Olefination / 5.2: |Wittig Olefination / 6.1: |Cross Metathesis;
DOI:10.1016/j.tet.2014.02.072