(17S)-17,20-dimethyl-6-oxo-PGE₁ methyl ester

Base Information

• Chemical Name: (17S)-17,20-dimethyl-6-oxo-PGE₁ methyl ester
• CAS No.: 92052-55-6
• Molecular Formula: C₂₃H₃₈O₆
• Molecular Weight: 410.551
• Mol file: 92052-55-6.mol

Synonyms:

Chemical Property of (17S)-17,20-dimethyl-6-oxo-PGE₁ methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (17S)-17,20-dimethyl-6-oxo-PGE₁ methyl ester

There total 13 articles about (17S)-17,20-dimethyl-6-oxo-PGE₁ 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: 93.0%

Ornoprostil bis-tert-butyldimethylsiloxy ether (92052-54-5) → (17S)-17,20-dimethyl-6-oxo-PGE1 methyl ester (70667-26-4,85679-51-2,92052-55-6)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In acetonitrile; for 4h; Ambient temperature;

DOI:10.1039/P19960000715

Reference yield:

6-(trimethylsilyl)hex-5-ynoic acid: (101224-43-5) → (17S)-17,20-dimethyl-6-oxo-PGE1 methyl ester (70667-26-4,85679-51-2,92052-55-6)

Guidance literature:

Multi-step reaction with 6 steps

1: conc. H₂SO₄ / 10 h / Ambient temperature

2: 1.) (c-C₆H₁₁)2BH, 2.) aq. NaOH / 2.) Pd(PPh₃)4 / 1.) THF, r.t., 1 h, 2.) benzene, 65 deg C, 1 h

3: 70percent m-CPBA / CH₂Cl₂ / 1 h / Ambient temperature

4: BF₃*Et₂O, MeOH / 0.5 h / 0 °C

5: 1.) t-BuLi, 2-thienyl(cyano)copper lithium / 1.) pentane, Et₂O, -78 deg C, 30 min; THF, -78 deg C, 30 min, 2.) -78 deg C, 1 h

6: 93 percent / HF*pyridine, pyridine / acetonitrile / 4 h / Ambient temperature

With pyridine; methanol; sodium hydroxide; 2-thienyl(cyano)copper lithium; sulfuric acid; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; tert.-butyl lithium; pyridine hydrogenfluoride; 3-chloro-benzenecarboperoxoic acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; acetonitrile;

DOI:10.1039/P19960000715

Reference yield:

(3S,4R)-3-(Methoxymethyloxy)-2-methylidene-4-(tert-butyldimethylsiloxy)cyclopentanone (117253-98-2) → (17S)-17,20-dimethyl-6-oxo-PGE1 methyl ester (70667-26-4,85679-51-2,92052-55-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / NaBr, BF₃*Et₂O / acetone / 0.5 h / Ambient temperature

2: 1.) (c-C₆H₁₁)2BH, 2.) aq. NaOH / 2.) Pd(PPh₃)4 / 1.) THF, r.t., 1 h, 2.) benzene, 65 deg C, 1 h

3: 70percent m-CPBA / CH₂Cl₂ / 1 h / Ambient temperature

4: BF₃*Et₂O, MeOH / 0.5 h / 0 °C

5: 1.) t-BuLi, 2-thienyl(cyano)copper lithium / 1.) pentane, Et₂O, -78 deg C, 30 min; THF, -78 deg C, 30 min, 2.) -78 deg C, 1 h

6: 93 percent / HF*pyridine, pyridine / acetonitrile / 4 h / Ambient temperature

With pyridine; methanol; sodium hydroxide; 2-thienyl(cyano)copper lithium; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; tert.-butyl lithium; pyridine hydrogenfluoride; 3-chloro-benzenecarboperoxoic acid; sodium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; acetone; acetonitrile;

DOI:10.1039/P19960000715

upstream raw materials:

Ornoprostil bis-tert-butyldimethylsiloxy ether

6-(trimethylsilyl)hex-5-ynoic acid:

(3S,4R)-3-(Methoxymethyloxy)-2-methylidene-4-(tert-butyldimethylsiloxy)cyclopentanone

(R)-4-(tert-Butyldimethylsiloxy)-2-(6-methoxycarbonylhexan-2-on-1-yl)cyclopent-2-enone