(R,5E,9Z,12Z)-2-(tert-butyldiphenylsilyloxy)-14-hydroxy-1-(4-methoxybenzyloxy)-9,12-dimethyltetradeca-5,9,12-trien-4-one

Base Information

Chemical Name:(R,5E,9Z,12Z)-2-(tert-butyldiphenylsilyloxy)-14-hydroxy-1-(4-methoxybenzyloxy)-9,12-dimethyltetradeca-5,9,12-trien-4-one
CAS No.:1453486-62-8
Molecular Formula:C₄₀H₅₂O₅Si
Molecular Weight:640.935
Hs Code.:

Synonyms:(R,5E,9Z,12Z)-2-(tert-butyldiphenylsilyloxy)-14-hydroxy-1-(4-methoxybenzyloxy)-9,12-dimethyltetradeca-5,9,12-trien-4-one

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Chemical Property of (R,5E,9Z,12Z)-2-(tert-butyldiphenylsilyloxy)-14-hydroxy-1-(4-methoxybenzyloxy)-9,12-dimethyltetradeca-5,9,12-trien-4-one

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Technology Process of (R,5E,9Z,12Z)-2-(tert-butyldiphenylsilyloxy)-14-hydroxy-1-(4-methoxybenzyloxy)-9,12-dimethyltetradeca-5,9,12-trien-4-one

There total 12 articles about (R,5E,9Z,12Z)-2-(tert-butyldiphenylsilyloxy)-14-hydroxy-1-(4-methoxybenzyloxy)-9,12-dimethyltetradeca-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: 83.0%

: 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

: 1453486-62-8
(R,5E,9Z,12Z)-2-(tert-butyldiphenylsilyloxy)-14-hydroxy-1-(4-methoxybenzyloxy)-9,12-dimethyltetradeca-5,9,12-trien-4-one

Guidance literature:: With (R)-10-camphorsulfonic acid; In methanol; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1016/j.tetasy.2013.07.002

Reference yield:

: 1453486-56-0
methyl (R)-3-(tert-butyldiphenylsilyloxy)-4-(4-methoxybenzyloxy)butanoate

: 1453486-62-8
(R,5E,9Z,12Z)-2-(tert-butyldiphenylsilyloxy)-14-hydroxy-1-(4-methoxybenzyloxy)-9,12-dimethyltetradeca-5,9,12-trien-4-one

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 1.5 h / Inert atmosphere

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

3.1: (R)-10-camphorsulfonic acid / methanol / 4 h / 20 °C / Inert atmosphere

With n-butyllithium; barium hydroxide octahydrate; (R)-10-camphorsulfonic acid; In tetrahydrofuran; methanol; hexane; water; 2.1: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1016/j.tetasy.2013.07.002

Reference yield:

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

: 1453486-62-8
(R,5E,9Z,12Z)-2-(tert-butyldiphenylsilyloxy)-14-hydroxy-1-(4-methoxybenzyloxy)-9,12-dimethyltetradeca-5,9,12-trien-4-one

Guidance literature:: Multi-step reaction with 2 steps

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

2: (R)-10-camphorsulfonic acid / methanol / 4 h / 20 °C / Inert atmosphere

With barium hydroxide octahydrate; (R)-10-camphorsulfonic acid; In tetrahydrofuran; methanol; water; 1: |Horner-Wadsworth-Emmons Olefination;
DOI:10.1016/j.tetasy.2013.07.002