(E)-ethyl 4-(3',5'-bis((tert-butyldimethylsilyl)oxy)-3-methoxy-4-(tosyloxy)-[1,10-biphenyl]-2-yl)-2-methylbut-2-enoate

Base Information

• Chemical Name: (E)-ethyl 4-(3',5'-bis((tert-butyldimethylsilyl)oxy)-3-methoxy-4-(tosyloxy)-[1,10-biphenyl]-2-yl)-2-methylbut-2-enoate
• CAS No.: 1443526-60-0
• Molecular Formula: C₃₉H₅₆O₈SSi₂
• Molecular Weight: 741.106

Synonyms:(E)-ethyl 4-(3',5'-bis((tert-butyldimethylsilyl)oxy)-3-methoxy-4-(tosyloxy)-[1,10-biphenyl]-2-yl)-2-methylbut-2-enoate

Chemical Property of (E)-ethyl 4-(3',5'-bis((tert-butyldimethylsilyl)oxy)-3-methoxy-4-(tosyloxy)-[1,10-biphenyl]-2-yl)-2-methylbut-2-enoate

Chemical Property:

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Technology Process of (E)-ethyl 4-(3',5'-bis((tert-butyldimethylsilyl)oxy)-3-methoxy-4-(tosyloxy)-[1,10-biphenyl]-2-yl)-2-methylbut-2-enoate

There total 7 articles about (E)-ethyl 4-(3',5'-bis((tert-butyldimethylsilyl)oxy)-3-methoxy-4-(tosyloxy)-[1,10-biphenyl]-2-yl)-2-methylbut-2-enoate 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: 98.0%

((5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-phenylene)bis(oxy))bis(tert-butyldimethylsilane) (1366234-66-3) + (E)-ethyl 4-(6-bromo-2-methoxy-3-(tosyloxy)phenyl)-2-methylbut-2-enoate (1443526-59-7) → (E)-ethyl 4-(3',5'-bis((tert-butyldimethylsilyl)oxy)-3-methoxy-4-(tosyloxy)-[1,10-biphenyl]-2-yl)-2-methylbut-2-enoate (1443526-60-0)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; In water; toluene; at 90 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tet.2013.05.007

Reference yield:

6-bromo-3-hydroxy-2-methoxybenzaldehyde (214123-07-6) → (E)-ethyl 4-(3',5'-bis((tert-butyldimethylsilyl)oxy)-3-methoxy-4-(tosyloxy)-[1,10-biphenyl]-2-yl)-2-methylbut-2-enoate (1443526-60-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 0 - 20 °C / Inert atmosphere

2: potassium tert-butylate / tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere

3: hydrogenchloride / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere; Reflux

4: dichloromethane / 1 h / 20 °C / Inert atmosphere

5: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; toluene / 24 h / 90 °C / Inert atmosphere

With 1H-imidazole; hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; potassium tert-butylate; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; toluene; 2: |Wittig Olefination / 6: |Suzuki-Miyaura Coupling;

DOI:10.1016/j.tet.2013.05.007

Reference yield:

C14H21BrO3Si → (E)-ethyl 4-(3',5'-bis((tert-butyldimethylsilyl)oxy)-3-methoxy-4-(tosyloxy)-[1,10-biphenyl]-2-yl)-2-methylbut-2-enoate (1443526-60-0)

Guidance literature:

Multi-step reaction with 5 steps

1: potassium tert-butylate / tetrahydrofuran / 2.5 h / 0 - 20 °C / Inert atmosphere

2: hydrogenchloride / tetrahydrofuran; water / 3 h / 20 °C / Inert atmosphere; Reflux

3: dichloromethane / 1 h / 20 °C / Inert atmosphere

4: triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

5: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate / water; toluene / 24 h / 90 °C / Inert atmosphere

With hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; potassium tert-butylate; triethylamine; In tetrahydrofuran; dichloromethane; water; toluene; 1: |Wittig Olefination / 5: |Suzuki-Miyaura Coupling;

DOI:10.1016/j.tet.2013.05.007

upstream raw materials:

6-bromo-3-hydroxy-2-methoxybenzaldehyde

2-(6-bromo-3-hydroxy-2-methoxyphenyl)acetaldehyde

(carbethoxyethylidene)triphenylphosphorane

(E)-ethyl 4-(6-bromo-3-hydroxy-2-methoxyphenyl)-2-methylbut-2-enoate

Downstream raw materials:

(R)-6,8-dihydroxy-1-methoxy-9-(prop-1-en-2-yl)-9,10-dihydrophenanthren-2-yl 4-methylbenzenesulfonate

(E)-3’,5’-dihydroxy-3-methoxy-2-(4-((methoxycarbonyl)oxy)-3-methylbut-2-en-1-yl)-[1,1'-biphenyl]-4-yl 4-methylbenzenesulfonate

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