(2E,4Z)-((S,E)-1-(4-methoxybenzyloxy)-4-methyl-5-((2S,6R)-6-(2-oxoethyl)-tetrahydro-2H-pyran-2-yl)pent-4-en-2-yl)-8-(diethoxyphosphoryl)-5-methyl-7-oxo octa-2,4-dienoate

Base Information

Chemical Name:(2E,4Z)-((S,E)-1-(4-methoxybenzyloxy)-4-methyl-5-((2S,6R)-6-(2-oxoethyl)-tetrahydro-2H-pyran-2-yl)pent-4-en-2-yl)-8-(diethoxyphosphoryl)-5-methyl-7-oxo octa-2,4-dienoate
CAS No.:1227307-32-5
Molecular Formula:C₃₄H₄₉O₁₀P
Molecular Weight:648.731
Hs Code.:

(2E,4Z)-((S,E)-1-(4-methoxybenzyloxy)-4-methyl-5-((2S,6R)-6-(2-oxoethyl)-tetrahydro-2H-pyran-2-yl)pent-4-en-2-yl)-8-(diethoxyphosphoryl)-5-methyl-7-oxo octa-2,4-dienoate

Synonyms:(2E,4Z)-((S,E)-1-(4-methoxybenzyloxy)-4-methyl-5-((2S,6R)-6-(2-oxoethyl)-tetrahydro-2H-pyran-2-yl)pent-4-en-2-yl)-8-(diethoxyphosphoryl)-5-methyl-7-oxo octa-2,4-dienoate

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Chemical Property of (2E,4Z)-((S,E)-1-(4-methoxybenzyloxy)-4-methyl-5-((2S,6R)-6-(2-oxoethyl)-tetrahydro-2H-pyran-2-yl)pent-4-en-2-yl)-8-(diethoxyphosphoryl)-5-methyl-7-oxo octa-2,4-dienoate

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Technology Process of (2E,4Z)-((S,E)-1-(4-methoxybenzyloxy)-4-methyl-5-((2S,6R)-6-(2-oxoethyl)-tetrahydro-2H-pyran-2-yl)pent-4-en-2-yl)-8-(diethoxyphosphoryl)-5-methyl-7-oxo octa-2,4-dienoate

There total 17 articles about (2E,4Z)-((S,E)-1-(4-methoxybenzyloxy)-4-methyl-5-((2S,6R)-6-(2-oxoethyl)-tetrahydro-2H-pyran-2-yl)pent-4-en-2-yl)-8-(diethoxyphosphoryl)-5-methyl-7-oxo octa-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: 72.0%

: 1227307-31-4
(2E,4Z)-((2S,E)-5-((2S,6R)-6-(2-hydroxyethyl)tetrahydro-2H-pyran-2-yl)-1-(4-methoxybenzyloxy)-4-methylpent-4-en-2-yl) 8-(diethoxyphosphoryl)-7-hydroxy-5-methylocta-2,4-dienoate

: 1227307-32-5
(2E,4Z)-((S,E)-1-(4-methoxybenzyloxy)-4-methyl-5-((2S,6R)-6-(2-oxoethyl)-tetrahydro-2H-pyran-2-yl)pent-4-en-2-yl)-8-(diethoxyphosphoryl)-5-methyl-7-oxo octa-2,4-dienoate

Guidance literature:: With Dess-Martin periodane; In dichloromethane; 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

: 1227307-32-5
(2E,4Z)-((S,E)-1-(4-methoxybenzyloxy)-4-methyl-5-((2S,6R)-6-(2-oxoethyl)-tetrahydro-2H-pyran-2-yl)pent-4-en-2-yl)-8-(diethoxyphosphoryl)-5-methyl-7-oxo octa-2,4-dienoate

Guidance literature:: Multi-step reaction with 6 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

5.1: pyridine hydrogenfluoride / tetrahydrofuran / 20 h / 0 - 20 °C

6.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C

With n-butyllithium; 2,4,6-trichlorobenzoyl chloride; water; Dess-Martin periodane; pyridine hydrogenfluoride; 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:

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

: 1227307-32-5
(2E,4Z)-((S,E)-1-(4-methoxybenzyloxy)-4-methyl-5-((2S,6R)-6-(2-oxoethyl)-tetrahydro-2H-pyran-2-yl)pent-4-en-2-yl)-8-(diethoxyphosphoryl)-5-methyl-7-oxo octa-2,4-dienoate

Guidance literature:: Multi-step reaction with 9 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 / 1 h / 20 °C

7.2: 18 h / Sonication

8.1: pyridine hydrogenfluoride / tetrahydrofuran / 20 h / 0 - 20 °C

9.1: Dess-Martin periodane / dichloromethane / 3 h / 20 °C

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