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

Base Information

Chemical Name:(2E,4Z)-((2S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 7-(tert-butyldimethylsilyloxy)-8-(diethoxyphosphoryl)-5-methylocta-2,4-dienoate
CAS No.:1227307-26-7
Molecular Formula:C₅₇H₈₅O₁₀PSi₂
Molecular Weight:1017.44
Hs Code.:

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

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

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

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

There total 23 articles about (2E,4Z)-((2S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 7-(tert-butyldimethylsilyloxy)-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: 85.0%

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

: 1227307-09-6
(S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-ol

: 1227307-26-7
(2E,4Z)-((2S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 7-(tert-butyldimethylsilyloxy)-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 1.5h; Inert atmosphere;

(S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-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:

: 1227307-15-4
(Z)-diethyl 2-hydroxy-6-(4-methoxy benzyloxy)-4-methyl hex-4-enyl phosphonate

: 1227307-26-7
(2E,4Z)-((2S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 7-(tert-butyldimethylsilyloxy)-8-(diethoxyphosphoryl)-5-methylocta-2,4-dienoate

Guidance literature:: Multi-step reaction with 5 steps

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

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1.67 h / 0 °C

2.2: 0.67 h / -78 °C

2.3: 1.75 h / -78 - 20 °C

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

3.2: 1.5 h / 0 °C

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

5.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene; acetonitrile / 1.5 h / 20 °C

5.2: 18 h / 20 °C

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; acetonitrile; 2.2: |Swern Oxidation / 2.3: |Swern Oxidation;
DOI:10.1002/chem.201202553

Reference yield:

: 1227307-14-3
(Z)-1-chloro-6-(4-methoxybenzyloxy)-4-methylhex-4-en-2-ol

: 1227307-26-7
(2E,4Z)-((2S,E)-5-((2S,6R)-6-(2-(tert-butyldiphenylsilyloxy)ethyl)-4-methylenetetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 7-(tert-butyldimethylsilyloxy)-8-(diethoxyphosphoryl)-5-methylocta-2,4-dienoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: potassium hydroxide / ethanol / 20 h / 0 °C

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

2.2: 6 h / -78 °C

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

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1.67 h / 0 °C

4.2: 0.67 h / -78 °C

4.3: 1.75 h / -78 - 20 °C

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

5.2: 1.5 h / 0 °C

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

7.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / toluene; acetonitrile / 1.5 h / 20 °C

7.2: 18 h / 20 °C

With dmap; n-butyllithium; 2,4,6-trichlorobenzoyl chloride; water; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hydroxide; sodium hydroxide; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 4.2: |Swern Oxidation / 4.3: |Swern Oxidation;
DOI:10.1002/chem.201202553