5-trans-PGF2alpha

Base Information

• Chemical Name: 5-trans-PGF2alpha
• CAS No.: 36150-01-3
• Molecular Formula: C20H34 O5
• Molecular Weight: 354.487
• UNII: EM5T9R5FAS
• DSSTox Substance ID: DTXSID501317801
• Nikkaji Number: J1.068.163D
• Wikidata: Q63398817
• Metabolomics Workbench ID: 2438
• Mol file: 36150-01-3.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 5-trans-PGF2alpha

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:

99% ,98%,Electron Grade , ^*data from raw suppliers

5-trans Prostaglandin F2α ≥99% ^*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

Technology Process of 5-trans-PGF2alpha

There total 71 articles about 5-trans-PGF2alpha 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:

C32H62O5Si2 + C32H62O5Si2 → dinoprost (551-11-1) + 5-trans-PGF2α (36150-01-3)

Guidance literature:

With hydrogenchloride; water; In tetrahydrofuran; at 20 ℃; for 0.5h;

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

upstream raw materials:

Prostaglandin G₂

(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