7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester

Base Information

• Chemical Name: 7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester
• CAS No.: 261772-00-3
• Molecular Formula: C₃₇H₆₄O₆Si₂
• Molecular Weight: 661.083

Synonyms:7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester

Chemical Property of 7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester

There total 13 articles about 7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic 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: 70.0%

7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester (41138-69-6) + 3-(S)-tert-butyldimethylsilyloxy-1-iodo-4-(3-methoxymethyl)phenyl-1-butene (253350-40-2) → 7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester (261772-00-3)

Guidance literature:

3-(S)-tert-butyldimethylsilyloxy-1-iodo-4-(3-methoxymethyl)phenyl-1-butene; With tert.-butyl lithium; In diethyl ether; pentane; at -70 ℃; for 1h;

7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester; With thien-2-yl(cyano)copper lithium; In tetrahydrofuran; diethyl ether; pentane; at -70 - -20 ℃;

DOI:10.1016/S0968-0896(02)00031-7

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester (261772-00-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 97 percent / imidazole / dimethylformamide / 20 °C

2.1: Cp₂ZrClH / tetrahydrofuran / 0.75 h / 20 °C

2.2: 80 percent / I₂ / tetrahydrofuran / 0.25 h / 0 °C

3.1: t-BuLi / diethyl ether; pentane / 1 h / -70 °C

3.2: 70 percent / lithium 2-thienylcyanocuprate / diethyl ether; pentane; tetrahydrofuran / -70 - -20 °C

With 1H-imidazole; Schwartz's reagent; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; pentane;

DOI:10.1016/S0968-0896(02)00031-7

Reference yield:

(3S)-4-(3-methoxymethylphenyl)-1-butyn-3-ol (253350-38-8) → 7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester (261772-00-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 97 percent / imidazole / dimethylformamide / 20 °C

2.1: Cp₂ZrClH / tetrahydrofuran / 0.75 h / 20 °C

2.2: 80 percent / I₂ / tetrahydrofuran / 0.25 h / 0 °C

3.1: t-BuLi / diethyl ether; pentane / 1 h / -70 °C

3.2: 70 percent / lithium 2-thienylcyanocuprate / diethyl ether; pentane; tetrahydrofuran / -70 - -20 °C

With 1H-imidazole; Schwartz's reagent; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; pentane;

DOI:10.1016/S0968-0896(02)00031-7

upstream raw materials:

7-{3-[(tert-butyldimethylsilanyl)oxy]-5-oxocyclopent-1-en-1-yl}heptanoic acid methyl ester

3-(S)-tert-butyldimethylsilyloxy-1-iodo-4-(3-methoxymethyl)phenyl-1-butene

3-(methoxymethyl)bromobenzene

tert-butyldimethylsilyl chloride

Downstream raw materials:

7-[(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-(toluene-4-sulfonyloxy)-cyclopentyl]-heptanoic acid methyl ester

7-{(1R,2R,3R,5R)-5-Chloro-3-hydroxy-2-[(E)-(S)-3-hydroxy-4-(3-methoxymethyl-phenyl)-but-1-enyl]-cyclopentyl}-heptanoic acid methyl ester

7-{(1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-hydroxy-cyclopentyl}-heptanoic acid methyl ester

7-{(1R,2R,3R)-3-Hydroxy-2-[(E)-(S)-3-hydroxy-4-(3-methoxymethyl-phenyl)-but-1-enyl]-5-oxo-cyclopentyl}-heptanoic acid methyl ester

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