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

Base Information

• Chemical Name: 7-((1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-but-1-enyl}-5-hydroxy-cyclopentyl)-heptanoic acid methyl ester
• CAS No.: 443147-49-7
• Molecular Formula: C₄₂H₇₈O₆Si₃
• Molecular Weight: 763.334
• Mol file: 443147-49-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about 7-((1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-but-1-enyl}-5-hydroxy-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: 74.0%

7-(3-(tert-butyl-dimethyl-silanyloxy)-2-{3-(tert-butyl-dimethyl-silanyloxy)-4-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-but-1-enyl}-5-oxo-cyclopentyl)-heptanoic acid methyl ester (443147-40-8) → 7-((1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-but-1-enyl}-5-hydroxy-cyclopentyl)-heptanoic acid methyl ester (443147-49-7)

Guidance literature:

With L-Selectride; In tetrahydrofuran; at -70 ℃;

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

Reference yield:

4-bromo-2-methyl-1-(2'-tetrahydropyranyloxy)benzene (148344-51-8) → 7-((1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-but-1-enyl}-5-hydroxy-cyclopentyl)-heptanoic acid methyl ester (443147-49-7)

Guidance literature:

Multi-step reaction with 13 steps

1.1: Mg; CuI / tetrahydrofuran / 0 °C

1.2: 100 percent / tetrahydrofuran

2.1: AcOH; H₂O / tetrahydrofuran / 65 °C

3.1: 2,4,6-collidine / CH₂Cl₂ / -78 °C

4.1: p-TsOH*H₂O / CH₂Cl₂ / 20 °C

5.1: 51 percent / 2N NaOH / methanol / 20 °C

6.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -70 - -30 °C

7.1: PPh₃; Et₃N / CH₂Cl₂ / -40 °C

8.1: n-BuLi / tetrahydrofuran; hexane / -70 °C

9.1: 85 percent / p-TsOH*H₂O / methanol / 20 °C

10.1: 100 percent / imidazole / dimethylformamide / 20 °C

11.1: Cp₂ZrClH / tetrahydrofuran / 20 °C

11.2: 93 percent / I₂ / tetrahydrofuran / 0 °C

12.1: t-BuLi / diethyl ether; pentane / -70 °C

12.2: 61 percent / lithium 2-thienylcyanocuprate / diethyl ether; pentane; tetrahydrofuran / -70 - -20 °C

13.1: 74 percent / L-selectride / tetrahydrofuran / -70 °C

With 1H-imidazole; 2,4,6-trimethyl-pyridine; sodium hydroxide; copper(l) iodide; Schwartz's reagent; n-butyllithium; oxalyl dichloride; water; tert.-butyl lithium; L-Selectride; toluene-4-sulfonic acid; magnesium; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; pentane;

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

Reference yield:

3-(S)-hydroxy-4-(4-hydroxy-3-methylphenyl)-1-butyne (443147-28-2) → 7-((1R,2R,3R,5S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-{(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-4-[4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-phenyl]-but-1-enyl}-5-hydroxy-cyclopentyl)-heptanoic acid methyl ester (443147-49-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / imidazole / dimethylformamide / 20 °C

2.1: Cp₂ZrClH / tetrahydrofuran / 20 °C

2.2: 93 percent / I₂ / tetrahydrofuran / 0 °C

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

3.2: 61 percent / lithium 2-thienylcyanocuprate / diethyl ether; pentane; tetrahydrofuran / -70 - -20 °C

4.1: 74 percent / L-selectride / tetrahydrofuran / -70 °C

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

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

upstream raw materials:

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

4-bromo-2-methyl-1-(2'-tetrahydropyranyloxy)benzene

3-(S)-hydroxy-4-(4-hydroxy-3-methylphenyl)-1-butyne

2-(S)-tetrahydropyranyloxy-3-(4-tetrahydropyranyloxy-3-methylphenyl)propan-1-al

Downstream raw materials:

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