11-epi-Prostaglandin F2alpha

Base Information

• Chemical Name: 11-epi-Prostaglandin F2alpha
• CAS No.: 38432-87-0
• Molecular Formula: C₂₀H₃₄O₅
• Molecular Weight: 354.487
• UNII: JG7TH29T3N
• ChEMBL ID: CHEMBL1369536
• DSSTox Substance ID: DTXSID50331533
• Metabolomics Workbench ID: 2402
• Nikkaji Number: J401.553C
• Wikidata: Q27103213
• Mol file: 38432-87-0.mol

Synonyms:9alpha,11beta PGF2;9alpha,11beta-PGF2;alpha, PGF2;Dinoprost;Enzaprost F;Estrofan;F2 alpha, Prostaglandin;F2alpha, Prostaglandin;PGF2;PGF2 alpha;PGF2alpha;Prostaglandin F2;Prostaglandin F2 alpha;Prostaglandin F2alpha

Chemical Property of 11-epi-Prostaglandin F2alpha

Chemical Property:

• Boiling Point: 531.0±50.0 °C(Predicted)
• PKA: 4.76±0.10(Predicted)
• PSA: 97.99000
• Density: 1.153±0.06 g/cm3(Predicted)
• LogP: 3.04290
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 354.24062418
• Heavy Atom Count: 25
• Complexity: 432

Purity/Quality:

98%Min ^*data from raw suppliers

11β-Prostaglandin F2α ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC(C1CC=CCCCC(=O)O)O)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@H](C[C@@H]([C@@H]1C/C=C\CCCC(=O)O)O)O)O
• Uses: 9alpha,11beta-PGF2 (9alpha,11beta-Prostaglandin F2) is platelet aggregation and adipose differentiation inhibitor.

Technology Process of 11-epi-Prostaglandin F2alpha

There total 78 articles about 11-epi-Prostaglandin F2alpha 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: 57.0%

C15H26O4 + (4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → prostaglandin F2α (551-11-1,4510-16-1,13164-29-9,23518-25-4,23518-26-5,27415-26-5,28977-22-2,36150-01-3,36150-02-4,37658-84-7,38310-95-1,38432-87-0,39762-37-3,42586-88-9,51262-67-0,51830-20-7,51830-21-8,52521-76-3,54324-23-1,54324-24-2,54324-25-3,54483-31-7,54483-32-8,57759-78-1,57759-79-2,57759-85-0,58717-39-8,59727-54-7,61046-31-9,61302-52-1,62446-65-5,64395-46-6,65026-00-8,65026-01-9,88391-39-3,88391-40-6,99880-86-1,117558-80-2,118456-51-2,123123-44-4,125411-82-7,146388-90-1)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1038/nature11411

Reference yield:

(3aR,6aS)-2-methoxy-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde → prostaglandin F2α (551-11-1,4510-16-1,13164-29-9,23518-25-4,23518-26-5,27415-26-5,28977-22-2,36150-01-3,36150-02-4,37658-84-7,38310-95-1,38432-87-0,39762-37-3,42586-88-9,51262-67-0,51830-20-7,51830-21-8,52521-76-3,54324-23-1,54324-24-2,54324-25-3,54483-31-7,54483-32-8,57759-78-1,57759-79-2,57759-85-0,58717-39-8,59727-54-7,61046-31-9,61302-52-1,62446-65-5,64395-46-6,65026-00-8,65026-01-9,88391-39-3,88391-40-6,99880-86-1,117558-80-2,118456-51-2,123123-44-4,125411-82-7,146388-90-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / tetrahydrofuran

2.1: ozone / methanol; dichloromethane / -78 °C

2.2: -78 - 20 °C

3.1: hydrogenchloride / tetrahydrofuran; water / 16 h / 20 °C

4.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C

With hydrogenchloride; potassium tert-butylate; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1038/nature11411

Reference yield:

(3aR,6aS)-2-hydroxy-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde → prostaglandin F2α (551-11-1,4510-16-1,13164-29-9,23518-25-4,23518-26-5,27415-26-5,28977-22-2,36150-01-3,36150-02-4,37658-84-7,38310-95-1,38432-87-0,39762-37-3,42586-88-9,51262-67-0,51830-20-7,51830-21-8,52521-76-3,54324-23-1,54324-24-2,54324-25-3,54483-31-7,54483-32-8,57759-78-1,57759-79-2,57759-85-0,58717-39-8,59727-54-7,61046-31-9,61302-52-1,62446-65-5,64395-46-6,65026-00-8,65026-01-9,88391-39-3,88391-40-6,99880-86-1,117558-80-2,118456-51-2,123123-44-4,125411-82-7,146388-90-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: magnesium sulfate / dichloromethane / 14 h / 20 °C

2.1: triethylamine / tetrahydrofuran

3.1: ozone / methanol; dichloromethane / -78 °C

3.2: -78 - 20 °C

4.1: hydrogenchloride / tetrahydrofuran; water / 16 h / 20 °C

5.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C

With hydrogenchloride; potassium tert-butylate; magnesium sulfate; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1038/nature11411

upstream raw materials:

11-epi-PGF_2α methyl ester

methyl (Z)-7-<(1R,2R,3R,5S)-5-tert-butyldimethylsilyloxy-2-<(tetrahydro-2-pyranyloxy)metyl>-3-hydroxycyclopentyl>-5-heptenoate

methyl (Z)-7-<(1R,2R,3R,5S)-5-tert-butyldimethylsilyloxy-2-<(tetrahydro-2-pyranyloxy)metyl>-3-methylsulfonyloxycyclopentyl>-5-heptenoate

methyl (Z)-7-<(1R,2R,3S,5S)-2-<(tetrahydro-2-pyranyloxy)methyl>-3,5-dihydroxycyclopentyl>-5-heptenoate

Refernces

• 1、 Mahrwald, Rainer,Schick, Hans,Pivnitsky, Kasimir K.,Schwarz, Sigfrid. "Prostaglandins and Prostaglandin Intermediates. Part 26 A Novel Route to PGF2α using Triisopropoxy-hept-1-ynyl-titanium as Precursor for the β-Side Chain". . p. 403 - 413. Retrieved 2007/10/02.
• 2、 Marino, Joseph P.,Pradilla, Roberto F. de la,Laborde, Edgardo. "Regio- and Stereoselectivity of the Reaction between Cyanocuprates and Cyclopentene Epoxides. Application to the Total Synthesis of Prostaglandins". . p. 4898 - 4913. Retrieved 2007/10/02.