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

Base Information

• Chemical Name: 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
• CAS No.: 438581-47-6
• Molecular Formula: C₄₈H₆₆O₉Si₂
• Molecular Weight: 843.218
• Mol file: 438581-47-6.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 12 articles about 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 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:

5-[3-(2-methoxyethoxymethoxy)propyl]-6-methyl-3-oxo-hept-6-enoic acid methyl ester (438581-46-5) + benzoic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-iodo-1-trimethylsilanyl-but-2-ynyl ester (438581-51-2) → 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)

Guidance literature:

5-[3-(2-methoxyethoxymethoxy)propyl]-6-methyl-3-oxo-hept-6-enoic acid methyl ester; With sodium hydride; In tetrahydrofuran; hexane; at 0 - 5 ℃; for 0.25h;

benzoic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-iodo-1-trimethylsilanyl-but-2-ynyl ester; In tetrahydrofuran; hexane; for 12h; Further stages.;

DOI:10.1021/ol025861m

Reference yield:

1-iodo-2-<(tert-butyldiphenylsilyl)oxy>ethane (126822-71-7) → 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)

Guidance literature:

Multi-step reaction with 6 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

With aluminum oxide; n-butyllithium; sodium hydride; ferric nitrate; triethylamine; sodium iodide; magnesium bromide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; acetone;

DOI:10.1021/ol025861m

Reference yield:

4-(2-methoxy-ethoxymethoxy)-butyraldehyde (273219-45-7) → 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)

Guidance literature:

Multi-step reaction with 6 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

With dmap; lithium hydroxide; sodium hydride; diisobutylaluminium hydride; propionic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; 1.1: Wittig reaction / 3.1: Johnson ortho ester-Claisen rearrangement;

DOI:10.1021/ol025861m

upstream raw materials:

5-[3-(2-methoxyethoxymethoxy)propyl]-6-methyl-3-oxo-hept-6-enoic acid methyl ester

benzoic acid 1-[2-(tert-butyl-diphenyl-silanyloxy)-ethyl]-4-iodo-1-trimethylsilanyl-but-2-ynyl ester

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

4-(2-methoxy-ethoxymethoxy)-butyraldehyde

Downstream raw materials:

(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