Methyl 15-hydroxy-9-oxoprosta-5,10,13-trien-1-oate

Base Information

• Chemical Name: Methyl 15-hydroxy-9-oxoprosta-5,10,13-trien-1-oate
• CAS No.: 31753-19-2
• Molecular Formula: C21H32O4
• Molecular Weight: 348.483
• DSSTox Substance ID: DTXSID70693968
• Wikidata: Q82622967
• Mol file: 31753-19-2.mol

Synonyms:DTXSID70693968;Prosta-5,10,13-trien-1-oic acid, 15-hydroxy-9-oxo-, methyl ester, (5Z,13E,15S)-;5-Heptenoic acid, 7-[2-(3-hydroxy-1-octenyl)-5-oxo-3-cyclopenten-1-yl]-, methyl ester, stereoisomer;Methyl 15-hydroxy-9-oxoprosta-5,10,13-trien-1-oate

Chemical Property of Methyl 15-hydroxy-9-oxoprosta-5,10,13-trien-1-oate

Chemical Property:

• Boiling Point: 477.4±45.0 °C(Predicted)
• PKA: 14.36±0.20(Predicted)
• PSA: 63.60000
• Density: 1.060±0.06 g/cm3(Predicted)
• LogP: 4.14470
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 13
• Exact Mass: 348.23005950
• Heavy Atom Count: 25
• Complexity: 490

Purity/Quality:

99% ^*data from raw suppliers

Prostaglandin A2 methyl ester ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1C=CC(=O)C1CC=CCCCC(=O)OC)O

Technology Process of Methyl 15-hydroxy-9-oxoprosta-5,10,13-trien-1-oate

There total 19 articles about Methyl 15-hydroxy-9-oxoprosta-5,10,13-trien-1-oate 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: 100.0%

prostaglandin A2 (13345-50-1) → (5Z,13E)-15-hydroxy-9-oxoprosta 5,10,13 trien-1-oic acid (31753-19-2)

Guidance literature:

With diazomethane; In diethyl ether;

DOI:10.1021/jo00134a011

Reference yield: 88.0%

prostaglandin A2 (13345-50-1) + methyl iodide (74-88-4) → (5Z,13E)-15-hydroxy-9-oxoprosta 5,10,13 trien-1-oic acid (31753-19-2)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 40h;

DOI:10.1021/ol0606583

Reference yield: 83.0%

Methyl (5Z,13E,8R,11R,12R,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(anti-oximino)-5,13-prostadienoate (85453-69-6) → (5Z,13E)-15-hydroxy-9-oxoprosta 5,10,13 trien-1-oic acid (31753-19-2) + prostaglandin E2 (31753-17-0)

Guidance literature:

With formaldehyd; boron trifluoride diethyl etherate; In water; acetone; for 120h; Ambient temperature;

DOI:10.1021/jo00161a010

upstream raw materials:

diazomethane

prostaglandin A₂

Methyl (5Z,13E,8R,11R,12R,15S)-11,15-Bis(tert-butyldimethylsiloxy)-9-(anti-oximino)-5,13-prostadienoate

methyl iodide

Downstream raw materials:

l-prostaglandin B₂ methyl ester

15α-O-t-butyldimethylsilyl-PGA₂ methyl ester

l-11-deoxy-11α-<(2-hydroxyethyl)thio>prostaglandin E₂ methyl ester

l-11-deoxy-11β-<(2-hydroxyethyl)thio>prostaglandin E₂ methyl ester