16-phenoxy tetranor Prostaglandin F2alpha

Base Information

• Chemical Name: 16-phenoxy tetranor Prostaglandin F2alpha
• CAS No.: 51705-19-2
• Molecular Formula: C22H30O6
• Molecular Weight: 390.47
• UNII: 5I3HIL901K
• Wikidata: Q27896410
• Pharos Ligand ID: 9HCAU1WUN2CQ
• ChEMBL ID: CHEMBL334398
• Mol file: 51705-19-2.mol

Synonyms:16-phenoxy tetranor Prostaglandin F2alpha;51705-19-2;5I3HIL901K;UNII-5I3HIL901K;CHEMBL334398;(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]cyclopentyl]hept-5-enoic acid;16-Phenoxy-17,18,19,20-tetranorprostaglandin F2alpha;16-phenoxy tetranor Prostaglandin F2.alpha.;5-Heptenoic acid, 7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((1E,3R)-3-hydroxy-4-phenoxy-1-buten-1-yl)cyclopentyl)-, (5Z)-;(+)-16-Phenoxy-17,18,19,20-tetranorprostaglandin F2alpha;PGF2Alpha,16-Phenoxy;SCHEMBL3368364;FAPQZCFUFGJPFI-UEAHRUCRSA-N;HMS3648H04;BDBM50106547;AKOS040756163;16-Phenoxy-Omega-Tetranor PGF-2alpha;16-phenoxy tetranor Prostaglandin F2??;PD021292;SR-01000946502;SR-01000946502-1;Q27896410;16-PHENOXY-17,18,19,20-TETRANORPROSTAGLANDIN F2.ALPHA.;(+)-16-PHENOXY-17,18,19,20-TETRANORPROSTAGLANDIN F2.ALPHA.;7-[3,5-Dihydroxy-2-(3-hydroxy-4-phenoxy-but-1-enyl)-cyclopentyl]-hept-5-enoic acid;9.alpha.,11.alpha.,15R-Trihydroxy-16-phenoxy-17,18,19,20-tetranor-prosta-5Z,13E-dien-1-oic acid

Chemical Property of 16-phenoxy tetranor Prostaglandin F2alpha

Chemical Property:

• PSA: 107.22000
• LogP: 2.54160
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 390.20423867
• Heavy Atom Count: 28
• Complexity: 511

Purity/Quality:

99% ^*data from raw suppliers

16-phenoxy tetranor Prostaglandin F2α ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C1O)C=CC(COC2=CC=CC=C2)O)CC=CCCCC(=O)O)O
• Isomeric SMILES: C1[C@@H]([C@@H]([C@H]([C@@H]1O)/C=C/[C@H](COC2=CC=CC=C2)O)C/C=C\CCCC(=O)O)O
• Description: 16-phenoxy PGF2α is a metabolically stable analog of PGF2α. It binds to the FP receptor on ovine luteal cells with much greater affinity (440%) than PGF2α.

Technology Process of 16-phenoxy tetranor Prostaglandin F2alpha

There total 1 articles about 16-phenoxy tetranor 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:

→ 16-phenoxy-omega-tetranor-PGF2 alpha (51705-19-2,40665-67-6)

Guidance literature:

entspr. 11,15-Bis-THP-ether, HCl;

Reference yield: 80.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + 16-phenoxy-omega-tetranor-PGF2 alpha (51705-19-2,40665-67-6) → 16-phenoxy-17,18,19,20-tetranorprostaglandin F2α methyl ester (51638-90-5,54348-08-2)

Guidance literature:

In diethyl ether;

DOI:10.1021/jm990542v

Reference yield:

16-phenoxy-omega-tetranor-PGF2 alpha (51705-19-2,40665-67-6) → 7-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-((R)-3-hydroxy-4-phenoxy-butyl)-cyclopentyl]-heptanoic acid

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / diethyl ether

2: 74 percent / H₂ / Pd/C / ethyl acetate

3: 85 percent / LiOH / tetrahydrofuran; H₂O / 20 °C

With lithium hydroxide; hydrogen; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; water; ethyl acetate; 1: Esterification / 2: Catalytic hydrogenation / 3: saponification;

DOI:10.1021/jm990542v

Downstream raw materials:

16-phenoxy-17,18,19,20-tetranorprostaglandin F_2α methyl ester

16-phenoxytetranorprostaglandin F_2α triacetate

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