(2E,4Z)-((S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 7-(tert-butyl dimethyl silyloxy)-8-(diethoxyphosphoryl)-5-methylocta-2,4-dienoate

Base Information

Chemical Name:(2E,4Z)-((S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 7-(tert-butyl dimethyl silyloxy)-8-(diethoxyphosphoryl)-5-methylocta-2,4-dienoate
CAS No.:1227307-30-3
Molecular Formula:C₅₆H₈₅O₁₀PSi₂
Molecular Weight:1005.43
Hs Code.:

(2E,4Z)-((S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 7-(tert-butyl dimethyl silyloxy)-8-(diethoxyphosphoryl)-5-methylocta-2,4-dienoate

Synonyms:(2E,4Z)-((S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 7-(tert-butyl dimethyl silyloxy)-8-(diethoxyphosphoryl)-5-methylocta-2,4-dienoate

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Chemical Property of (2E,4Z)-((S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 7-(tert-butyl dimethyl silyloxy)-8-(diethoxyphosphoryl)-5-methylocta-2,4-dienoate

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Technology Process of (2E,4Z)-((S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 7-(tert-butyl dimethyl silyloxy)-8-(diethoxyphosphoryl)-5-methylocta-2,4-dienoate

There total 14 articles about (2E,4Z)-((S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 7-(tert-butyl dimethyl silyloxy)-8-(diethoxyphosphoryl)-5-methylocta-2,4-dienoate 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: 74.0%

: 1227307-08-5
(2E,4Z)-7-((tert-butyldimethylsilyl)oxy)-8-(diethoxyphosphoryl)-5-methylocta-2,4-dienoic acid

: 1227307-18-7
(S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy-)ethyl-)tetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-ol

: 1227307-30-3
(2E,4Z)-((S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 7-(tert-butyl dimethyl silyloxy)-8-(diethoxyphosphoryl)-5-methylocta-2,4-dienoate

Guidance literature:: (2E,4Z)-7-((tert-butyldimethylsilyl)oxy)-8-(diethoxyphosphoryl)-5-methylocta-2,4-dienoic acid; With 2,4,6-trichlorobenzoyl chloride; triethylamine; In toluene; at 20 ℃; for 1h; Inert atmosphere;

(S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy-)ethyl-)tetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-ol; With dmap; In toluene; at 20 ℃; Inert atmosphere;
DOI:10.1021/ol100665m

Reference yield:

: 1227307-24-5
(Z)-diethyl 2-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)-4-methylhex-4-enylphosphonate

: 1227307-30-3
(2E,4Z)-((S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 7-(tert-butyl dimethyl silyloxy)-8-(diethoxyphosphoryl)-5-methylocta-2,4-dienoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1.67 h / 0 °C

1.2: 0.67 h / -78 °C

1.3: 1.75 h / -78 - 20 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C

2.2: 1.5 h / 0 °C

3.1: water; sodium hydroxide / ethanol / 25 h / 0 - 20 °C

4.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 1 h / 20 °C

4.2: 18 h / Sonication

With n-butyllithium; 2,4,6-trichlorobenzoyl chloride; water; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; toluene; 1.2: |Swern Oxidation / 1.3: |Swern Oxidation;
DOI:10.1002/chem.201202553

Reference yield:

: 1227307-23-4
(Z)-2-(4-(4-methoxybenzyloxy)-2-methylbut-2-enyl)oxirane

: 1227307-30-3
(2E,4Z)-((S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 7-(tert-butyl dimethyl silyloxy)-8-(diethoxyphosphoryl)-5-methylocta-2,4-dienoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: 6 h / -78 °C

2.1: dmap / N,N-dimethyl-formamide / 36 h / 20 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1.67 h / 0 °C

3.2: 0.67 h / -78 °C

3.3: 1.75 h / -78 - 20 °C

4.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / 0 °C

4.2: 1.5 h / 0 °C

5.1: water; sodium hydroxide / ethanol / 25 h / 0 - 20 °C

6.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene / 1 h / 20 °C

6.2: 18 h / Sonication

With dmap; n-butyllithium; 2,4,6-trichlorobenzoyl chloride; water; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 3.2: |Swern Oxidation / 3.3: |Swern Oxidation;
DOI:10.1002/chem.201202553