(R,2Z,5Z,9E)-13-(tert-butyldiphenylsilyloxy)-14-(4-methoxybenzyloxy)-3,6-dimethyl-11-oxotetradeca-2,5,9-trienoic acid

Base Information

• Chemical Name: (R,2Z,5Z,9E)-13-(tert-butyldiphenylsilyloxy)-14-(4-methoxybenzyloxy)-3,6-dimethyl-11-oxotetradeca-2,5,9-trienoic acid
• CAS No.: 1453486-64-0
• Molecular Formula: C₄₀H₅₀O₆Si
• Molecular Weight: 654.919

Synonyms:(R,2Z,5Z,9E)-13-(tert-butyldiphenylsilyloxy)-14-(4-methoxybenzyloxy)-3,6-dimethyl-11-oxotetradeca-2,5,9-trienoic acid

Chemical Property of (R,2Z,5Z,9E)-13-(tert-butyldiphenylsilyloxy)-14-(4-methoxybenzyloxy)-3,6-dimethyl-11-oxotetradeca-2,5,9-trienoic acid

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Technology Process of (R,2Z,5Z,9E)-13-(tert-butyldiphenylsilyloxy)-14-(4-methoxybenzyloxy)-3,6-dimethyl-11-oxotetradeca-2,5,9-trienoic acid

There total 14 articles about (R,2Z,5Z,9E)-13-(tert-butyldiphenylsilyloxy)-14-(4-methoxybenzyloxy)-3,6-dimethyl-11-oxotetradeca-2,5,9-trienoic acid 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: 89.0%

C40H50O5Si (1453486-63-9) → (R,2Z,5Z,9E)-13-(tert-butyldiphenylsilyloxy)-14-(4-methoxybenzyloxy)-3,6-dimethyl-11-oxotetradeca-2,5,9-trienoic acid (1453486-64-0)

Guidance literature:

With sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; at 20 ℃; for 0.5h; Inert atmosphere;

DOI:10.1016/j.tetasy.2013.07.002

Reference yield:

dimethyl (R)-4-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-2-oxopentylphosphonate (1453486-57-1) → (R,2Z,5Z,9E)-13-(tert-butyldiphenylsilyloxy)-14-(4-methoxybenzyloxy)-3,6-dimethyl-11-oxotetradeca-2,5,9-trienoic acid (1453486-64-0)

Guidance literature:

Multi-step reaction with 4 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

3: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

4: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0.5 h / 20 °C / Inert atmosphere

With sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; barium hydroxide octahydrate; (R)-10-camphorsulfonic acid; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; water; tert-butyl alcohol; 1: |Horner-Wadsworth-Emmons Olefination;

DOI:10.1016/j.tetasy.2013.07.002

Reference yield:

(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 (1453486-61-7) → (R,2Z,5Z,9E)-13-(tert-butyldiphenylsilyloxy)-14-(4-methoxybenzyloxy)-3,6-dimethyl-11-oxotetradeca-2,5,9-trienoic acid (1453486-64-0)

Guidance literature:

Multi-step reaction with 3 steps

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

2: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 20 °C / Inert atmosphere

3: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 0.5 h / 20 °C / Inert atmosphere

With sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; (R)-10-camphorsulfonic acid; sodium hydrogencarbonate; Dess-Martin periodane; In methanol; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/j.tetasy.2013.07.002

upstream raw materials:

methyl (R)-3-hydroxy-4-(4-methoxybenzyloxy)butanoate

dimethyl (R)-4-(tert-butyldiphenylsilyloxy)-5-(4-methoxybenzyloxy)-2-oxopentylphosphonate

methyl (R)-3-(tert-butyldiphenylsilyloxy)-4-(4-methoxybenzyloxy)butanoate

2-(((2Z,5Z)-9-((4-methoxybenzyl)oxy)-3,6-dimethylnona-2,5-dien-1-yl)oxy)tetrahydro-2H-pyran

Downstream raw materials:

(S,3Z,6Z,10E)-14-(((4-methoxybenzyl)oxy)methyl)-4,7-dimethyloxacyclotetradeca-3,6,10-triene-2,12-dione

C₂₄H₃₂O₆

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