(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

Base Information

Chemical Name:(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
CAS No.:1227307-31-4
Molecular Formula:C₃₄H₅₃O₁₀P
Molecular Weight:652.763
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 16 articles about (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 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: 80.0%

: 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

: 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

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; at 0 - 20 ℃; for 20.0833h; Inert atmosphere;
DOI:10.1021/ol100665m

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 5 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

With n-butyllithium; 2,4,6-trichlorobenzoyl chloride; water; 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:

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

: 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

Guidance literature:: Multi-step reaction with 7 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

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

With dmap; n-butyllithium; 2,4,6-trichlorobenzoyl chloride; water; pyridine hydrogenfluoride; 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