(Z)-5-[4-(tert-butyldiphenylsilanyloxy)-2-(trimethylsilanyl)-but-1-enyl]-2-{2-[3-(2-methoxyethoxymethoxy)propyl]-3-methyl-but-3-enyl}furan-3-carboxylic acid methyl ester

Base Information

• Chemical Name: (Z)-5-[4-(tert-butyldiphenylsilanyloxy)-2-(trimethylsilanyl)-but-1-enyl]-2-{2-[3-(2-methoxyethoxymethoxy)propyl]-3-methyl-but-3-enyl}furan-3-carboxylic acid methyl ester
• CAS No.: 438581-48-7
• Molecular Formula: C₄₁H₆₀O₇Si₂
• Molecular Weight: 721.094
• Mol file: 438581-48-7.mol

Synonyms:(Z)-5-[4-(tert-butyldiphenylsilanyloxy)-2-(trimethylsilanyl)-but-1-enyl]-2-{2-[3-(2-methoxyethoxymethoxy)propyl]-3-methyl-but-3-enyl}furan-3-carboxylic acid methyl ester

Chemical Property of (Z)-5-[4-(tert-butyldiphenylsilanyloxy)-2-(trimethylsilanyl)-but-1-enyl]-2-{2-[3-(2-methoxyethoxymethoxy)propyl]-3-methyl-but-3-enyl}furan-3-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-5-[4-(tert-butyldiphenylsilanyloxy)-2-(trimethylsilanyl)-but-1-enyl]-2-{2-[3-(2-methoxyethoxymethoxy)propyl]-3-methyl-but-3-enyl}furan-3-carboxylic acid methyl ester

There total 14 articles about (Z)-5-[4-(tert-butyldiphenylsilanyloxy)-2-(trimethylsilanyl)-but-1-enyl]-2-{2-[3-(2-methoxyethoxymethoxy)propyl]-3-methyl-but-3-enyl}furan-3-carboxylic acid methyl ester 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:

benzoic acid 1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-5-methoxycarbonyl-8-[3-(2-methoxyethoxymethoxy)propyl]-9-methyl-6-oxo-1-(trimethylsilanyl)dec-9-en-2-ynyl ester (438581-47-6) → (Z)-5-[4-(tert-butyldiphenylsilanyloxy)-2-(trimethylsilanyl)-but-1-enyl]-2-{2-[3-(2-methoxyethoxymethoxy)propyl]-3-methyl-but-3-enyl}furan-3-carboxylic acid methyl ester (438581-48-7)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; potassium carbonate; In water; acetonitrile; at 82 ℃; for 24h;

DOI:10.1021/ol025861m

Reference yield:

1-iodo-2-<(tert-butyldiphenylsilyl)oxy>ethane (126822-71-7) → (Z)-5-[4-(tert-butyldiphenylsilanyloxy)-2-(trimethylsilanyl)-but-1-enyl]-2-{2-[3-(2-methoxyethoxymethoxy)propyl]-3-methyl-but-3-enyl}furan-3-carboxylic acid methyl ester (438581-48-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 2 h / -20 °C

1.2: tetrahydrofuran; hexane / -78 - 20 °C

2.1: 0.493 g / iron(III) nitrate nonahydrate; basic alumina / hexane / 1 h / 43 °C

3.1: n-butyllithium / diethyl ether; hexane / 0.17 h / -78 °C

3.2: 71 percent / diethyl ether; hexane / 0.17 h / -78 °C

4.1: 80 percent / triethylamine; magnesium bromide / CH₂Cl₂ / 3 h / 20 °C

5.1: sodium iodide / acetone / 1 h / 60 °C

6.1: sodium hydride / tetrahydrofuran; hexane / 0.25 h / 0 - 5 °C

6.2: tetrahydrofuran; hexane / 12 h

7.1: K₂CO₃; Pd(OAc)2; dppf / acetonitrile; H₂O / 24 h / 82 °C

With aluminum oxide; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; n-butyllithium; sodium hydride; potassium carbonate; ferric nitrate; triethylamine; sodium iodide; magnesium bromide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; acetone; acetonitrile;

DOI:10.1021/ol025861m

Reference yield:

4-(2-methoxy-ethoxymethoxy)-butyraldehyde (273219-45-7) → (Z)-5-[4-(tert-butyldiphenylsilanyloxy)-2-(trimethylsilanyl)-but-1-enyl]-2-{2-[3-(2-methoxyethoxymethoxy)propyl]-3-methyl-but-3-enyl}furan-3-carboxylic acid methyl ester (438581-48-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1.50 g / CH₂Cl₂ / 2 h

2.1: 83 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.17 h / -78 °C

3.1: 81 percent / propionic acid / 7 h / 143 °C

4.1: lithium hydroxide monohydrate / ethanol; H₂O / 19 h

5.1: 1,3-dicyclohexylcarbodiimide; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h

5.2: 0.321 g / 20 h / 68 °C

6.1: sodium hydride / tetrahydrofuran; hexane / 0.25 h / 0 - 5 °C

6.2: tetrahydrofuran; hexane / 12 h

7.1: K₂CO₃; Pd(OAc)2; dppf / acetonitrile; H₂O / 24 h / 82 °C

With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; lithium hydroxide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; propionic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; acetonitrile; 1.1: Wittig reaction / 3.1: Johnson ortho ester-Claisen rearrangement;

DOI:10.1021/ol025861m

upstream raw materials:

benzoic acid 1-[2-(tert-butyldiphenylsilanyloxy)ethyl]-5-methoxycarbonyl-8-[3-(2-methoxyethoxymethoxy)propyl]-9-methyl-6-oxo-1-(trimethylsilanyl)dec-9-en-2-ynyl ester

1-iodo-2-<(tert-butyldiphenylsilyl)oxy>ethane

4-(2-methoxy-ethoxymethoxy)-butyraldehyde

O-(methoxyethoxymethyl)-1,4-butanediol