17-trans Prostaglandin F3α

Base Information

• Chemical Name: 17-trans Prostaglandin F3α
• CAS No.: 211100-24-2
• Molecular Formula: C20H32O5
• Molecular Weight: 352.47
• Mol file: 211100-24-2.mol

Synonyms:17-trans Prostaglandin F3α

Chemical Property of 17-trans Prostaglandin F3α

Chemical Property:

• PSA: 97.99000
• LogP: 2.81890

Purity/Quality:

97% ^*data from raw suppliers

17-trans Prostaglandin F3α ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 17-trans PGF3α is a double bond isomer of PGF3α and a potential metabolite of trans dietary fatty acids. There are no published reports on the biological activity of this compound.

Technology Process of 17-trans Prostaglandin F3α

There total 18 articles about 17-trans Prostaglandin F3α 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、 -. "PGB3 analogs". . . Retrieved 2008/06/13.