Carbaprostacyclin methyl ester

Base Information

• Chemical Name: Carbaprostacyclin methyl ester
• CAS No.: 69552-55-2
• Molecular Formula: C22H36O4
• Molecular Weight: 364.52
• Mol file: 69552-55-2.mol

Synonyms:Carbaprostacyclin methyl ester

Chemical Property of Carbaprostacyclin methyl ester

Chemical Property:

• PSA: 66.76000
• LogP: 4.16050

Purity/Quality:

≥98% ^*data from raw suppliers

Carbaprostacyclin methyl ester ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Carbaprostacyclin methyl ester

There total 63 articles about Carbaprostacyclin 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: 100.0%

Methyl (1S,5S,6R,7R)-7-tert-Butyldimethylsilyloxy-6-<3(S)-tert-butyldimethylsilyloxy-E-1-octenyl>bicyclo<3.3.0>octane-E-Δ3,δ-pentanoate (98718-28-6) → (5E)-6a-carbaprostaglandin I2 methyl ester (69552-55-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 23 ℃; for 13h;

DOI:10.1248/cpb.39.309

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: 47.0%

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)

Guidance literature:

With lithium aluminium tetrahydride; ethanol; (S)-[1,1']-binaphthalenyl-2,2'-diol; In tetrahydrofuran; at -78 ℃; for 2h; Inert atmosphere;

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

Methyl (1S,5S,6R,7R)-7-tert-Butyldimethylsilyloxy-6-<3(S)-tert-butyldimethylsilyloxy-E-1-octenyl>bicyclo<3.3.0>octane-E-Δ^3,δ-pentanoate

3α,5α-dihydroxy-2β-(benzyloxymethyl)cyclopentane-1α-acetic acid γ-lactone 3-tetrahydropyran-2-yl ether

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

Downstream raw materials:

(5E)-carba-PGI2