(5E,16R)-6α-carbaprostaglandin I₂ methyl ester

Base Information

• Chemical Name: (5E,16R)-6α-carbaprostaglandin I₂ methyl ester
• CAS No.: 71884-06-5
• Molecular Formula: C₂₂H₃₆O₄
• Molecular Weight: 364.525
• Mol file: 71884-06-5.mol

Synonyms:

Chemical Property of (5E,16R)-6α-carbaprostaglandin I₂ methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5E,16R)-6α-carbaprostaglandin I₂ methyl ester

There total 29 articles about (5E,16R)-6α-carbaprostaglandin I₂ 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: 83.0%

Methyl (1S,5S,6R,7R)-7-Hydroxy-6-(3-oxo-E-1-octenyl)bicyclo<3.3.0>octane-E-Δ3.δ-pentanoate (71846-05-4) → (5E)-6a-carbaprostaglandin I2 methyl ester (69552-55-2) + (5E,16R)-6α-carbaprostaglandin I2 methyl ester (71884-06-5)

Guidance literature:

With 2,6-di-tert-butyl-4-methyl-phenol; diisobutylaluminium hydride; Yield given. Multistep reaction; 1.) toluene, 5 deg C, 1 h, 2.) toluene, -78 deg C (adding), up to -10 deg C within 2.5 h, then -10 deg C, 10 min;

DOI:10.1016/0040-4020(81)80005-1

Reference yield:

3α,5α-dihydroxy-2β-(benzyloxymethyl)cyclopentane-1α-acetic acid γ-lactone 3-tetrahydropyran-2-yl ether (32233-38-8) → (5E)-6a-carbaprostaglandin I2 methyl ester (69552-55-2) + (5E,16R)-6α-carbaprostaglandin I2 methyl ester (71884-06-5)

Guidance literature:

Multi-step reaction with 15 steps

1.1: sodium hydroxide; water / methanol / 0.5 h / 20 °C

2.1: diethyl ether; ethyl acetate / 5 °C

3.1: chromyl chloride; pyridine / dichloromethane; tert-butyl alcohol; tetrachloromethane / 2.5 h / 35 °C

4.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere

4.2: 2 h / -78 °C / Inert atmosphere

5.1: hydrogen; 5%-palladium/activated carbon / ethanol / 1.6 h / 20 °C / 760.05 Torr

6.1: potassium tert-butylate / benzene / 4 h / 70 °C / Inert atmosphere

6.2: 0.25 h / 175 °C

7.1: hydrogen; 5%-palladium/activated carbon / ethyl acetate / 96 h / 20 °C / 760.05 Torr

8.1: toluene-4-sulfonic acid / dichloromethane; tetrahydrofuran / 0.17 h / 10 °C

9.1: sodium methylsulfinylmethanide / dimethyl sulfoxide / 25 °C

9.2: 16 h / 35 °C

10.1: hydrogenchloride / tetrahydrofuran; water / 0.17 h / 0 °C

11.1: diethyl ether

12.1: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 0.25 h / 20 °C

13.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

13.2: 1 h / 20 °C / Inert atmosphere

14.1: acetic acid / tetrahydrofuran / 0.75 h / 50 °C

15.1: 2,6-di-tert-butyl-4-methyl-phenol; diisobutylaluminium hydride / toluene / 2.75 h / -78 - -10 °C / Inert atmosphere

With pyridine; hydrogenchloride; n-butyllithium; 2,6-di-tert-butyl-4-methyl-phenol; 5%-palladium/activated carbon; potassium tert-butylate; water; hydrogen; sulfur trioxide pyridine complex; chromyl chloride; sodium hydride; diisobutylaluminium hydride; sodium methylsulfinylmethanide; toluene-4-sulfonic acid; acetic acid; triethylamine; diisopropylamine; sodium hydroxide; In tetrahydrofuran; methanol; tetrachloromethane; diethyl ether; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; tert-butyl alcohol; benzene; 6.1: |Dieckmann Condensation / 13.1: |Horner-Wadsworth-Emmons Olefination / 13.2: |Horner-Wadsworth-Emmons Olefination;

Reference yield:

methyl 3α-hydroxy-5-oxo-2β-(benzyloxymethyl)cyclopentane-1α-acetate 3-tetrahydropyran-2-yl ether (74163-85-2) → (5E)-6a-carbaprostaglandin I2 methyl ester (69552-55-2) + (5E,16R)-6α-carbaprostaglandin I2 methyl ester (71884-06-5)

Guidance literature:

Multi-step reaction with 12 steps

1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

2.1: hydrogen; 5%-palladium/activated carbon / ethanol / 1.6 h / 20 °C / 760.05 Torr

3.1: potassium tert-butylate / benzene / 4 h / 70 °C / Inert atmosphere

3.2: 0.25 h / 175 °C

4.1: hydrogen; 5%-palladium/activated carbon / ethyl acetate / 96 h / 20 °C / 760.05 Torr

5.1: toluene-4-sulfonic acid / dichloromethane; tetrahydrofuran / 0.17 h / 10 °C

6.1: sodium methylsulfinylmethanide / dimethyl sulfoxide / 25 °C

6.2: 16 h / 35 °C

7.1: hydrogenchloride / tetrahydrofuran; water / 0.17 h / 0 °C

8.1: diethyl ether

9.1: triethylamine; sulfur trioxide pyridine complex / dimethyl sulfoxide / 0.25 h / 20 °C

10.1: sodium hydride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

10.2: 1 h / 20 °C / Inert atmosphere

11.1: acetic acid / tetrahydrofuran / 0.75 h / 50 °C

12.1: 2,6-di-tert-butyl-4-methyl-phenol; diisobutylaluminium hydride / toluene / 2.75 h / -78 - -10 °C / Inert atmosphere

With hydrogenchloride; n-butyllithium; 2,6-di-tert-butyl-4-methyl-phenol; 5%-palladium/activated carbon; potassium tert-butylate; hydrogen; sulfur trioxide pyridine complex; sodium hydride; diisobutylaluminium hydride; sodium methylsulfinylmethanide; toluene-4-sulfonic acid; acetic acid; triethylamine; diisopropylamine; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; toluene; benzene; 3.1: |Dieckmann Condensation / 10.1: |Horner-Wadsworth-Emmons Olefination / 10.2: |Horner-Wadsworth-Emmons Olefination;

upstream raw materials:

Methyl (1S,5S,6R,7R)-7-Hydroxy-6-(3-oxo-E-1-octenyl)bicyclo<3.3.0>octane-E-Δ^3.δ-pentanoate

7-oxo-2β-benzyloxymethyl-3-bicyclo<3.3.0>octene

3α-hydroxy-4β-bromo-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane

3α-hydroxy-7-oxo-2β-hydroxymethylbicyclo<3.3.0>octane 3-tetrahydropyranyl ether