5-Trans Prostaglandin F2beta

Base Information

• Chemical Name: 5-Trans Prostaglandin F2beta
• CAS No.: 36150-02-4
• Molecular Formula: C₂₀H₃₄O₅
• Molecular Weight: 354.487
• DSSTox Substance ID: DTXSID701347755
• Mol file: 36150-02-4.mol

Synonyms:5-Trans Prostaglandin F2beta;36150-02-4;(E)-7-[(1R,2R,3R,5R)-3,5-dihydroxy-2-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid;9beta,11alpha,15S-Trihydroxy-prosta-5E,13E-dien-1-oic acid;5,6-trans PGF2beta;5-trans Prostaglandin F2 beta;DTXSID701347755;HMS3648B06;PD021086;SR-01000946474;SR-01000946474-1;Prosta-5,13-dien-1-oicacid,9,11,15-trihydroxy-,(5e,9b,11a,13e,15s)-;(5E,9beta,11alpha,13E,15S)-9,11,15-Trihydroxyprosta-5,13-dien-1-oic acid;(E)-7-((1R,2R,3R,5R)-3,5-dihydroxy-2-((S,E)-3-hydroxyoct-1-enyl)cyclopentyl)hept-5-enoic acid

Chemical Property of 5-Trans Prostaglandin F2beta

Chemical Property:

• PSA: 97.99000
• 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% ^*data from raw suppliers

5-trans Prostaglandin F2β ≥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: 5-trans PGF2α is the 9β-hydroxy isomer of 5-trans PGF2α. There are no published reports on the biological activity of this compound.

Technology Process of 5-Trans Prostaglandin F2beta

There total 69 articles about 5-Trans Prostaglandin F2beta 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:

(4-carboxybutyl)triphenylphosphonium bromide

(Z)-7-{(1S,2S,3S,5R)-2-[(E)-3-(tert-Butyl-dimethyl-silanyloxy)-oct-1-enyl]-5-hydroxy-3-methoxymethoxy-cyclopentyl}-hept-5-enoic acid

trans-4-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-2,3-epoxycyclopentanone

trans-4,5-epoxy-3-<(1E)-3-<(tert-butyldimethylsilyl)oxy>oct-1-enyl>-1-<(triethylsilyl)oxy>cyclopentene

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.