(2R,5E,9Z,12Z)-2-((tert-butyldiphenylsilyl)oxy)-1-((4-methoxybenzyl)oxy)-9,12-dimethyl-14-((tetrahydro-2H-pyran-2-yl)oxy)tetradeca-5,9,12-trien-4-one

Base Information

Chemical Name:(2R,5E,9Z,12Z)-2-((tert-butyldiphenylsilyl)oxy)-1-((4-methoxybenzyl)oxy)-9,12-dimethyl-14-((tetrahydro-2H-pyran-2-yl)oxy)tetradeca-5,9,12-trien-4-one
CAS No.:1453486-61-7
Molecular Formula:C₄₅H₆₀O₆Si
Molecular Weight:725.053
Hs Code.:

Synonyms:(2R,5E,9Z,12Z)-2-((tert-butyldiphenylsilyl)oxy)-1-((4-methoxybenzyl)oxy)-9,12-dimethyl-14-((tetrahydro-2H-pyran-2-yl)oxy)tetradeca-5,9,12-trien-4-one

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Chemical Property of (2R,5E,9Z,12Z)-2-((tert-butyldiphenylsilyl)oxy)-1-((4-methoxybenzyl)oxy)-9,12-dimethyl-14-((tetrahydro-2H-pyran-2-yl)oxy)tetradeca-5,9,12-trien-4-one

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Technology Process of (2R,5E,9Z,12Z)-2-((tert-butyldiphenylsilyl)oxy)-1-((4-methoxybenzyl)oxy)-9,12-dimethyl-14-((tetrahydro-2H-pyran-2-yl)oxy)tetradeca-5,9,12-trien-4-one

There total 11 articles about (2R,5E,9Z,12Z)-2-((tert-butyldiphenylsilyl)oxy)-1-((4-methoxybenzyl)oxy)-9,12-dimethyl-14-((tetrahydro-2H-pyran-2-yl)oxy)tetradeca-5,9,12-trien-4-one 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:

: 1453486-57-1
dimethyl (R)-4-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-2-oxopentylphosphonate

: 1453486-60-6
C₁₆H₂₆O₃

: 1453486-61-7
(2R,5E,9Z,12Z)-2-((tert-butyldiphenylsilyl)oxy)-1-((4-methoxybenzyl)oxy)-9,12-dimethyl-14-((tetrahydro-2H-pyran-2-yl)oxy)tetradeca-5,9,12-trien-4-one

Guidance literature:: With barium hydroxide octahydrate; In tetrahydrofuran; water; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1016/j.tetasy.2013.07.002

Reference yield:

: 1453486-55-9
methyl (R)-3-hydroxy-4-(4-methoxybenzyloxy)butanoate

: 1453486-61-7
(2R,5E,9Z,12Z)-2-((tert-butyldiphenylsilyl)oxy)-1-((4-methoxybenzyl)oxy)-9,12-dimethyl-14-((tetrahydro-2H-pyran-2-yl)oxy)tetradeca-5,9,12-trien-4-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 0.17 h / Inert atmosphere

1.2: 6 h / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -78 °C / Inert atmosphere

2.2: 1.5 h / Inert atmosphere

3.1: barium hydroxide octahydrate / tetrahydrofuran; water / 2 h / 20 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; barium hydroxide octahydrate; In tetrahydrofuran; hexane; water; N,N-dimethyl-formamide; 3.1: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1016/j.tetasy.2013.07.002

Reference yield:

: 475637-93-5
(Z)-2-((3-iodobut-2-en-1-yl)oxy)tetrahydro-2H-pyran

: 1453486-61-7
(2R,5E,9Z,12Z)-2-((tert-butyldiphenylsilyl)oxy)-1-((4-methoxybenzyl)oxy)-9,12-dimethyl-14-((tetrahydro-2H-pyran-2-yl)oxy)tetradeca-5,9,12-trien-4-one

Guidance literature:: Multi-step reaction with 4 steps

1.1: tert.-butyl lithium / diethyl ether; pentane / 0.5 h / -78 °C / Inert atmosphere

1.2: 0.25 h / -78 °C / Inert atmosphere

1.3: 1 h / 0 °C / Inert atmosphere

2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / pH 7 / Inert atmosphere

3.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.1: barium hydroxide octahydrate / tetrahydrofuran; water / 2 h / 20 °C / Inert atmosphere

With barium hydroxide octahydrate; tert.-butyl lithium; sodium hydrogencarbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; diethyl ether; dichloromethane; water; pentane; 1.3: |Negishi Coupling / 3.1: |Dess-Martin Oxidation / 4.1: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1016/j.tetasy.2013.07.002