4-(2-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-5-oxo-cyclopentyl}-ethyl)-benzoic acid methyl ester

Base Information

• Chemical Name: 4-(2-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-5-oxo-cyclopentyl}-ethyl)-benzoic acid methyl ester
• CAS No.: 433219-74-0
• Molecular Formula: C₃₇H₆₂O₅Si₂
• Molecular Weight: 643.067

Synonyms:

Chemical Property of 4-(2-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-5-oxo-cyclopentyl}-ethyl)-benzoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 4-(2-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-5-oxo-cyclopentyl}-ethyl)-benzoic acid methyl ester

There total 9 articles about 4-(2-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-5-oxo-cyclopentyl}-ethyl)-benzoic 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:

[(4-methoxycarbonylphenyl)methyl]zinc bromide + 4-(tert-butyl-dimethyl-silanyloxy)-3-[4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-2-methylene-cyclopentanone (433219-73-9) → 4-(2-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-5-oxo-cyclopentyl}-ethyl)-benzoic acid methyl ester (433219-74-0)

Guidance literature:

[(4-methoxycarbonylphenyl)methyl]zinc bromide; 4-(tert-butyl-dimethyl-silanyloxy)-3-[4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-2-methylene-cyclopentanone; With chloro-trimethyl-silane; In tetrahydrofuran; at -78 - -20 ℃; for 3h;

With pyridinium p-toluenesulfonate; In methanol; diethyl ether; at 20 ℃; for 1h;

DOI:10.1016/S0968-0896(01)00369-8

Reference yield:

Cyclobutanecarboxylic acid (3721-95-7) → 4-(2-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-5-oxo-cyclopentyl}-ethyl)-benzoic acid methyl ester (433219-74-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: lithium diisopropylamide / tetrahydrofuran / 12 h / 20 °C

2.1: LiAlH₄ / diethyl ether / 3.5 h / 20 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 1.5 h / -78 - 0 °C

4.1: Mg; mercuric chloride / diethyl ether / 0.17 h / 0 °C

4.2: diethyl ether / 1 h / 20 °C

5.1: 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 - 20 °C

6.1: n-Bu₃SnH; AIBN / 2 h / 80 °C

6.2: I₂ / diethyl ether / 0.17 h / 0 °C

7.1: t-BuLi; lithium 2-thienylcyanocuprate / diethyl ether; pentane; tetrahydrofuran / 1 h / -78 - 0 °C

8.1: CuCN*2LiCl; Me₃SiCl / tetrahydrofuran / 3 h / -78 - -20 °C

8.2: pyridinium p-toluenesulfonate / methanol; diethyl ether / 1 h / 20 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; chloro-trimethyl-silane; oxalyl dichloride; 2,2'-azobis(isobutyronitrile); tert.-butyl lithium; tri-n-butyl-tin hydride; magnesium; dimethyl sulfoxide; thien-2-yl(cyano)copper lithium; triethylamine; mercury dichloride; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; pentane; 3.1: Swern oxidation;

DOI:10.1016/S0968-0896(01)00369-8

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → 4-(2-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-5-oxo-cyclopentyl}-ethyl)-benzoic acid methyl ester (433219-74-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 2,6-lutidine / CH₂Cl₂ / 0.17 h / 0 - 20 °C

2.1: n-Bu₃SnH; AIBN / 2 h / 80 °C

2.2: I₂ / diethyl ether / 0.17 h / 0 °C

3.1: t-BuLi; lithium 2-thienylcyanocuprate / diethyl ether; pentane; tetrahydrofuran / 1 h / -78 - 0 °C

4.1: CuCN*2LiCl; Me₃SiCl / tetrahydrofuran / 3 h / -78 - -20 °C

4.2: pyridinium p-toluenesulfonate / methanol; diethyl ether / 1 h / 20 °C

With 2,6-dimethylpyridine; chloro-trimethyl-silane; 2,2'-azobis(isobutyronitrile); tert.-butyl lithium; tri-n-butyl-tin hydride; thien-2-yl(cyano)copper lithium; In tetrahydrofuran; diethyl ether; dichloromethane; pentane;

DOI:10.1016/S0968-0896(01)00369-8

upstream raw materials:

4-(tert-butyl-dimethyl-silanyloxy)-3-[4-(tert-butyl-dimethyl-silanyloxy)-4-(1-ethyl-cyclobutyl)-but-1-enyl]-2-methylene-cyclopentanone

Cyclobutanecarboxylic acid

t-butyldimethylsiyl triflate

1-ethylcyclobutanecarbaldehyde

Downstream raw materials:

4-(2-{(1R,2R,3R)-2-[(E)-(S)-4-(1-Ethyl-cyclobutyl)-4-hydroxy-but-1-enyl]-3-hydroxy-5-oxo-cyclopentyl}-ethyl)-benzoic acid methyl ester

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