(R,2E,4E)-6-((tert-butyldimethylsilyl)oxy)-7-(3,4-dimethoxyphenyl)hepta-2,4-dienoic acid

Base Information

• Chemical Name: (R,2E,4E)-6-((tert-butyldimethylsilyl)oxy)-7-(3,4-dimethoxyphenyl)hepta-2,4-dienoic acid
• CAS No.: 1448848-29-0
• Molecular Formula: C₂₁H₃₂O₅Si
• Molecular Weight: 392.568

Synonyms:(R,2E,4E)-6-((tert-butyldimethylsilyl)oxy)-7-(3,4-dimethoxyphenyl)hepta-2,4-dienoic acid

Chemical Property of (R,2E,4E)-6-((tert-butyldimethylsilyl)oxy)-7-(3,4-dimethoxyphenyl)hepta-2,4-dienoic acid

Chemical Property:

Purity/Quality:

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Technology Process of (R,2E,4E)-6-((tert-butyldimethylsilyl)oxy)-7-(3,4-dimethoxyphenyl)hepta-2,4-dienoic acid

There total 14 articles about (R,2E,4E)-6-((tert-butyldimethylsilyl)oxy)-7-(3,4-dimethoxyphenyl)hepta-2,4-dienoic 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: 95.0%

(R,2E,4E)-ethyl 6-((tert-butyldimethylsilyl)oxy)-7-(3,4-dimethoxyphenyl)hepta-2,4-dienoate (1448848-28-9) → (R,2E,4E)-6-((tert-butyldimethylsilyl)oxy)-7-(3,4-dimethoxyphenyl)hepta-2,4-dienoic acid (1448848-29-0)

Guidance literature:

With lithium hydroxide monohydrate; water; In tetrahydrofuran; methanol; at 20 ℃; for 6h; Inert atmosphere;

DOI:10.1039/c6md00606j

Reference yield:

(R,E)-4-((tert-butyldimethylsilyl)oxy)-5-(3,4-dimethoxyphenyl)pent-2-en-1-ol (1448848-26-7) → (R,2E,4E)-6-((tert-butyldimethylsilyl)oxy)-7-(3,4-dimethoxyphenyl)hepta-2,4-dienoic acid (1448848-29-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; dimethyl sulfoxide / dichloromethane / 3 h / 20 °C

2: benzene / 1 h / Reflux

3: lithium hydroxide monohydrate / tetrahydrofuran; water / 6 h / 20 °C

With lithium hydroxide monohydrate; dimethyl sulfoxide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; dichloromethane; water; benzene; 2: |Wittig Olefination;

DOI:10.1016/j.tetlet.2013.06.034

Reference yield:

C19H30O4Si (1448848-32-5) → (R,2E,4E)-6-((tert-butyldimethylsilyl)oxy)-7-(3,4-dimethoxyphenyl)hepta-2,4-dienoic acid (1448848-29-0)

Guidance literature:

Multi-step reaction with 2 steps

1: benzene / 1 h / Reflux

2: lithium hydroxide monohydrate / tetrahydrofuran; water / 6 h / 20 °C

With lithium hydroxide monohydrate; In tetrahydrofuran; water; benzene; 1: |Wittig Olefination;

DOI:10.1016/j.tetlet.2013.06.034

upstream raw materials:

(R,E)-ethyl-4-((tert-butyldimethylsilyl)oxy)-5-(3,4-dimethoxyphenyl)pent-2-enoate

(R,E)-4-((tert-butyldimethylsilyl)oxy)-5-(3,4-dimethoxyphenyl)pent-2-en-1-ol

C₁₉H₃₀O₄Si

(R,E)-ethyl5-(3,4-dimethoxyphenyl)-4-hydroxypent-2-enoate

Downstream raw materials:

(R,2E,4E)-6-((tert-Butyldimethylsilyl)oxy)-7-(3,4-dimethoxyphenyl)-N-ethylhepta-2,4-dienamide

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