(2R,3R,4R)-2-(3-(benzyloxy)benzyl)-4-triethylsilyloxy-3-((3S,1E)-3-triethylsilyloxyoct-1-enyl)cyclopentanone

Base Information

• Chemical Name: (2R,3R,4R)-2-(3-(benzyloxy)benzyl)-4-triethylsilyloxy-3-((3S,1E)-3-triethylsilyloxyoct-1-enyl)cyclopentanone
• CAS No.: 1425937-39-8
• Molecular Formula: C₃₉H₆₂O₄Si₂
• Molecular Weight: 651.09
• Mol file: 1425937-39-8.mol

Synonyms:(2R,3R,4R)-2-(3-(benzyloxy)benzyl)-4-triethylsilyloxy-3-((3S,1E)-3-triethylsilyloxyoct-1-enyl)cyclopentanone

Chemical Property of (2R,3R,4R)-2-(3-(benzyloxy)benzyl)-4-triethylsilyloxy-3-((3S,1E)-3-triethylsilyloxyoct-1-enyl)cyclopentanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R)-2-(3-(benzyloxy)benzyl)-4-triethylsilyloxy-3-((3S,1E)-3-triethylsilyloxyoct-1-enyl)cyclopentanone

There total 1 articles about (2R,3R,4R)-2-(3-(benzyloxy)benzyl)-4-triethylsilyloxy-3-((3S,1E)-3-triethylsilyloxyoct-1-enyl)cyclopentanone 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: 94.0%

(3R)-1-[3-(benzyloxy)benzyl]-5-oxo-3-(triethylsilyloxy)cyclopent-1-ene (1425937-59-2) + (1S,2E)-1-pentyl-3-(1,1,1-tributylstannyl)-2-propenyl (1,1,1-triethylsilyl) ether (183073-00-9) → (2R,3R,4R)-2-(3-(benzyloxy)benzyl)-4-triethylsilyloxy-3-((3S,1E)-3-triethylsilyloxyoct-1-enyl)cyclopentanone (1425937-39-8)

Guidance literature:

(1S,2E)-1-pentyl-3-(1,1,1-tributylstannyl)-2-propenyl (1,1,1-triethylsilyl) ether; With n-butyllithium; methyllithium; copper(l) cyanide; In tetrahydrofuran; diethyl ether; hexane; at -70 ℃; for 0.5h;

(3R)-1-[3-(benzyloxy)benzyl]-5-oxo-3-(triethylsilyloxy)cyclopent-1-ene; In tetrahydrofuran; diethyl ether; hexane; at -70 ℃; for 0.5h;

Reference yield:

(2R,3R,4R)-2-(3-(benzyloxy)benzyl)-4-triethylsilyloxy-3-((3S,1E)-3-triethylsilyloxyoct-1-enyl)cyclopentanone (1425937-39-8) → treprostinil (81846-19-7)

Guidance literature:

Multi-step reaction with 10 steps

1.1: toluene-4-sulfonic acid / tetrahydrofuran; dichloromethane / 1.5 h / 25 °C / Cooling with ice

1.2: 1 h / 20 °C

2.1: 1H-imidazole / ethyl acetate / 20 °C

3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 °C / Inert atmosphere

3.2: 1.75 h / 0 - 20 °C

4.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere

5.1: hydrogen; potassium hydroxide; 5%-palladium/activated carbon / methanol / 5 h

6.1: sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 °C / Inert atmosphere; Reflux

7.1: acetic acid / tetrahydrofuran; water / 20 °C

8.1: hydrogen; potassium hydroxide; 5%-palladium/activated carbon / methanol / 20 °C

9.1: potassium carbonate; tetrabutylammomium bromide / acetone / 30 °C

10.1: water; potassium hydroxide / methanol / 3 h / Reflux

10.2: pH 2

With 1H-imidazole; 5%-palladium/activated carbon; tetrabutylammomium bromide; water; hydrogen; sodium hydride; potassium carbonate; toluene-4-sulfonic acid; acetic acid; triethylamine; 9-bora-bicyclo[3.3.1]nonane; potassium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone; mineral oil;

Reference yield:

(2R,3R,4R)-2-(3-(benzyloxy)benzyl)-4-triethylsilyloxy-3-((3S,1E)-3-triethylsilyloxyoct-1-enyl)cyclopentanone (1425937-39-8) → (1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalene-2,5-diol (101692-02-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: toluene-4-sulfonic acid / tetrahydrofuran; dichloromethane / 1.5 h / 25 °C / Cooling with ice

1.2: 1 h / 20 °C

2.1: 1H-imidazole / ethyl acetate / 20 °C

3.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 0 °C / Inert atmosphere

3.2: 1.75 h / 0 - 20 °C

4.1: triethylamine / dichloromethane / 0 °C / Inert atmosphere

5.1: hydrogen; potassium hydroxide; 5%-palladium/activated carbon / methanol / 5 h

6.1: sodium hydride / tetrahydrofuran; mineral oil / 4 h / 0 °C / Inert atmosphere; Reflux

7.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 - 20 °C

7.2: 0.5 h

8.1: acetic acid / tetrahydrofuran; water / 20 °C

9.1: hydrogen; 5%-palladium/activated carbon / methanol / 5 h / 20 °C

10.1: sodium hydroxide / methanol / 1 h / 20 °C

With 1H-imidazole; 5%-palladium/activated carbon; hydrogen; sodium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; 9-bora-bicyclo[3.3.1]nonane; potassium hydroxide; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; mineral oil;

upstream raw materials:

(3R)-1-[3-(benzyloxy)benzyl]-5-oxo-3-(triethylsilyloxy)cyclopent-1-ene

(1S,2E)-1-pentyl-3-(1,1,1-tributylstannyl)-2-propenyl (1,1,1-triethylsilyl) ether

Downstream raw materials:

(1R,2R,3R)-3-(3-(benzyloxy)benzyl)-2-((3S,1E)-3-hydroxyoct-1-enyl)-4-methylenecyclopentanol

(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-(tert-butyldimethylsilyloxy)-1-((3S,1E)-3-(tert-butyl dimethylsilyloxy)oct-1-enyl)-1H-cyclopenta[b]naphthalen-5-yl benzoate

(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((3S,1E)-3-hydroxyoct-1-enyl)-1H-cyclopenta[b]naphthalen-5-yl benzoate

(1R,2R,3aS,9aS)-2,3,3a,4,9,9a-hexahydro-2-hydroxy-1-((S)-3-hydroxyoctyl)-1H-cyclopenta[b]naphthalen-5-yl benzoate

Refernces

• 1、 -. "Intermediates for the synthesis of benzindene prostaglandins and preparations thereof". Paragraph 0079; 0080; 0081; 0082. . Retrieved 2013/04/25.