Prostaglandin F3alpha

Base Information

• Chemical Name: Prostaglandin F3alpha
• CAS No.: 745-64-2
• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.471
• Metabolomics Workbench ID: 2480
• Nikkaji Number: J39.476I
• Wikidata: Q27104327
• Mol file: 745-64-2.mol

Synonyms:PGF3alpha;prostaglandin F3 alpha;prostaglandin F3alpha

Chemical Property of Prostaglandin F3alpha

Chemical Property:

• Vapor Pressure: 5.43E-14mmHg at 25°C
• Boiling Point: 541.7 °C at 760 mmHg
• PKA: 4.76±0.10(Predicted)
• Flash Point: 295.4 °C
• PSA: 97.99000
• Density: 1.171 g/cm³
• LogP: 2.81890
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 11
• Exact Mass: 352.22497412
• Heavy Atom Count: 25
• Complexity: 469

Purity/Quality:

98%Min ^*data from raw suppliers

Prostaglandin F3α ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC=CCC(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O
• Isomeric SMILES: CC/C=C\C[C@@H](/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O)O

Technology Process of Prostaglandin F3alpha

There total 18 articles about Prostaglandin F3alpha 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: 99.0%

PGF3α methyl ester (13261-26-2) → PGF3α (745-64-2,211100-24-2)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 4.5h;

DOI:10.1016/S0040-4020(01)88868-2

Reference yield:

(Z)-7-{(1R,2R,3R,5S)-5-Hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(1E,5Z)-(S)-3-(tetrahydro-pyran-2-yloxy)-octa-1,5-dienyl]-cyclopentyl}-hept-5-enoic acid (32233-50-4) → PGF3α (745-64-2,211100-24-2)

Guidance literature:

With acetic acid; In tetrahydrofuran;

DOI:10.1021/ja00735a032

Reference yield:

1-bromo-pent-2-yne (16400-32-1) → PGF3α (745-64-2,211100-24-2)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) Zn / 1.) THF, 2.) THF, 0 deg C, 1 h

2: 84 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / -30 - -20 °C

3: 67 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.) 0 deg C, 4 h, 2.) 20 deg C, 40 min

4: 77 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 24 h / 20 °C

5: 96 percent / NaOMe / methanol / 2 h / 20 °C

6: 67 percent / Jones reagent / acetone / 0.25 h / -20 °C

7: aq. AcOH / tetrahydrofuran / 4.5 h / 40 °C

8: 99 percent / H₂ / Lindlar catalyst / benzene; cyclohexane; cyclohexene / 0.33 h / 20 °C / 760 Torr

9: 46 percent / L-Selectride / tetrahydrofuran / 0.25 h / -78 °C

10: 99 percent / 0.6 M aq. NaOH / methanol / 4.5 h / 20 °C

With dmap; sodium hydroxide; jones reagent; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; pyridinium p-toluenesulfonate; L-Selectride; acetic acid; zinc; Lindlar's catalyst; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; acetone; cyclohexene; benzene;

DOI:10.1016/S0040-4020(01)88868-2

upstream raw materials:

(Z)-7-{(1R,2R,3R,5S)-5-Hydroxy-3-(tetrahydro-pyran-2-yloxy)-2-[(1E,5Z)-(S)-3-(tetrahydro-pyran-2-yloxy)-octa-1,5-dienyl]-cyclopentyl}-hept-5-enoic acid

PGF_3α methyl ester

1-bromo-pent-2-yne

PGE₃ methyl ester

Downstream raw materials:

(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((1E,5Z)-(S)-3-hydroxy-octa-1,5-dienyl)-cyclopentyl]-hept-5-enoic acid biphenyl-4-yloxycarbonylmethyl ester

Prostaglandin F(3α)-p-phenylbenzylester

(Z)-7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((1E,5Z)-(S)-3-hydroxy-octa-1,5-dienyl)-cyclopentyl]-hept-5-enoic acid 2-(2,5-dimethoxy-phenyl)-2-oxo-ethyl ester

Refernces

• 1、 Corey,Shirahama,Yamamoto,Terashima,Venkateswarlu,Schaaf. "Stereospecific total synthesis of prostaglandins E3 and F3 alpha.". . p. 1490 - 1491. Retrieved 2007/10/16.