(1S,2E,5S,8E,10Z,14E,17R)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-6,21-dioxabicyclo [15.3.1]henicosa-2,8,10,14-tetraene-7,13-dione

Base Information

Chemical Name:(1S,2E,5S,8E,10Z,14E,17R)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-6,21-dioxabicyclo [15.3.1]henicosa-2,8,10,14-tetraene-7,13-dione
CAS No.:1227307-19-8
Molecular Formula:C₃₀H₃₈O₆
Molecular Weight:494.628
Hs Code.:

Synonyms:(1S,2E,5S,8E,10Z,14E,17R)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-6,21-dioxabicyclo [15.3.1]henicosa-2,8,10,14-tetraene-7,13-dione

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Chemical Property of (1S,2E,5S,8E,10Z,14E,17R)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-6,21-dioxabicyclo [15.3.1]henicosa-2,8,10,14-tetraene-7,13-dione

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Technology Process of (1S,2E,5S,8E,10Z,14E,17R)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-6,21-dioxabicyclo [15.3.1]henicosa-2,8,10,14-tetraene-7,13-dione

There total 18 articles about (1S,2E,5S,8E,10Z,14E,17R)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-6,21-dioxabicyclo [15.3.1]henicosa-2,8,10,14-tetraene-7,13-dione 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%

: 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

: 1227307-19-8
(1S,2E,5S,8E,10Z,14E,17R)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-6,21-dioxabicyclo [15.3.1]henicosa-2,8,10,14-tetraene-7,13-dione

Guidance literature:: With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 - 20 ℃; for 48h; Inert atmosphere;
DOI:10.1021/ol100665m

Reference yield:

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

: 1227307-19-8
(1S,2E,5S,8E,10Z,14E,17R)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-6,21-dioxabicyclo [15.3.1]henicosa-2,8,10,14-tetraene-7,13-dione

Guidance literature:: Multi-step reaction with 7 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

7.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 48 h / -78 - 20 °C

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

: 1227307-19-8
(1S,2E,5S,8E,10Z,14E,17R)-5-((4-methoxybenzyloxy)methyl)-3,11-dimethyl-6,21-dioxabicyclo [15.3.1]henicosa-2,8,10,14-tetraene-7,13-dione

Guidance literature:: Multi-step reaction with 10 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

10.1: sodium hexamethyldisilazane / tetrahydrofuran; toluene / 48 h / -78 - 20 °C

With dmap; n-butyllithium; 2,4,6-trichlorobenzoyl chloride; water; sodium hexamethyldisilazane; 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