(E)-1-[(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)methoxy]-2-(triisopropylsilyloxymethyl)but-2-ene

Base Information

• Chemical Name: (E)-1-[(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)methoxy]-2-(triisopropylsilyloxymethyl)but-2-ene
• CAS No.: 1441119-47-6
• Molecular Formula: C₃₂H₄₈O₈Si
• Molecular Weight: 588.814
• Mol file: 1441119-47-6.mol

Synonyms:(E)-1-[(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)methoxy]-2-(triisopropylsilyloxymethyl)but-2-ene

Chemical Property of (E)-1-[(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)methoxy]-2-(triisopropylsilyloxymethyl)but-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-1-[(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)methoxy]-2-(triisopropylsilyloxymethyl)but-2-ene

There total 4 articles about (E)-1-[(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)methoxy]-2-(triisopropylsilyloxymethyl)but-2-ene 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: 66.0%

[7-methoxy-6-(3,4,5-trimethoxyphenyl)-benzo[1,3]dioxol-5-yl]methanol (870094-81-8) + (Z)-1-bromo-2-(triisopropylsilyloxymethyl)but-2-ene (1044749-61-2) → (E)-1-[(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)methoxy]-2-(triisopropylsilyloxymethyl)but-2-ene (1441119-47-6)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.1002/ejoc.201201247

Reference yield:

6-bromo-7-methoxybenzo[1,3]dioxole-5-carboxylic acid ethyl ester (418755-58-5) → (E)-1-[(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)methoxy]-2-(triisopropylsilyloxymethyl)but-2-ene (1441119-47-6)

Guidance literature:

Multi-step reaction with 3 steps

1: diisobutylaluminium hydride / toluene / -78 °C

2: CyJohnPhos; potassium phosphate; palladium diacetate / toluene / 80 °C / Inert atmosphere

3: potassium tert-butylate / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

With potassium phosphate; potassium tert-butylate; palladium diacetate; diisobutylaluminium hydride; CyJohnPhos; In tetrahydrofuran; toluene; 2: |Suzuki Coupling / 3: |Williamson Ether Synthesis;

DOI:10.1002/ejoc.201201247

Reference yield:

ethyl (3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)carboxylate (1441119-45-4) → (E)-1-[(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)methoxy]-2-(triisopropylsilyloxymethyl)but-2-ene (1441119-47-6)

Guidance literature:

Multi-step reaction with 2 steps

1: diisobutylaluminium hydride / hexane; toluene / 1.5 h / -78 °C / Inert atmosphere

2: potassium tert-butylate / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

With potassium tert-butylate; diisobutylaluminium hydride; In tetrahydrofuran; hexane; toluene; 2: |Williamson Ether Synthesis;

DOI:10.1002/ejoc.201201247

upstream raw materials:

[7-methoxy-6-(3,4,5-trimethoxyphenyl)-benzo[1,3]dioxol-5-yl]methanol

(Z)-1-bromo-2-(triisopropylsilyloxymethyl)but-2-ene

ethyl (3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)carboxylate

3,4,5-trimethoxyphenylboronic Acid

Downstream raw materials:

(1R,2S)-2-methyl-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)-3-[(triisopropylsilyloxy)methyl]but-3-en-1-ol

(1R,2S)-2-methyl-3-methylene-1-(3',4',5',6-tetramethoxy-4,5-methylenedioxybiphenyl-2-yl)butane-1,4-diol

(-)-eupomatilone 1