15-epi-Prostaglandin E2

Base Information

• Chemical Name: 15-epi-Prostaglandin E2
• CAS No.: 38873-82-4
• Molecular Formula: C₂₀H₃₂O₅
• Molecular Weight: 352.471
• UNII: T3D76GXW94
• DSSTox Substance ID: DTXSID801017284
• Nikkaji Number: J1.567.582I
• Wikidata: Q27289615
• Pharos Ligand ID: GCFUDBXVTSZL
• Metabolomics Workbench ID: 2449
• ChEMBL ID: CHEMBL64804
• Mol file: 38873-82-4.mol

Synonyms:15(R)-Prostaglandin E2;15-epi-Prostaglandin E2;38873-82-4;15-epi-Dinoprostone;15-Epiprostaglandin E2;(15R)-Prostaglandin E2;UNII-T3D76GXW94;Dinoprostone impurity A [EP];T3D76GXW94;15R-Prostaglandin E2;15beta-PGE2;CHEMBL64804;15R-PGE2;8,15-diepi-15-E2t-IsoP;Dinoprostone impurity, 15-epi-dinoprostone- [USP];(Z)-7-((1R,2R,3R)-3-Hydroxy-2-((E)-(3R)-3-hydroxyoct-1-enyl)-5-oxocyclopentyl)hept-5-enoic;(Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxyoct-1-enyl]-5-oxocyclopentyl]hept-5-enoic acid;9-oxo-11R,15R-dihydroxy-5Z,13E-prostadienoic acid;9-oxo-11R,15R-dihydroxy-5Z,13E-prostadienoic acid-cyclo[8R,12R];9-Oxo-11alpha,15R-dihydroxy-prosta-5Z,13E-dien-1-oic acid;PGE2, 15-epi;15.BETA.-PGE2;SCHEMBL23352819;DTXSID801017284;HMS3648H17;BDBM50101822;LMFA03010094;PD021131;DINOPROSTONE IMPURITY A [EP IMPURITY];SR-01000946430;SR-01000946430-1;Q27289615;DINOPROSTONE IMPURITY, 15-EPI-DINOPROSTONE- [USP IMPURITY];(Z)-7-[(1R,2R,3R)-3-Hydroxy-2-((E)-(R)-3-hydroxy-oct-1-enyl)-5-oxo-cyclopentyl]-hept-5-enoic acid

Chemical Property of 15-epi-Prostaglandin E2

Chemical Property:

• PSA: 94.83000
• LogP: 3.25110
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 352.22497412
• Heavy Atom Count: 25
• Complexity: 469

Purity/Quality:

99% ^*data from raw suppliers

15(R)-Prostaglandin E2 ≥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)O)O)O
• Isomeric SMILES: CCCCC[C@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1C/C=C\CCCC(=O)O)O)O
• Uses: 15(R)?-?Prostaglandin E2 is a prostaglandins in the gorgonian Plexaura homomalla. 15(R)?-?Prostaglandin E2 isan isomeric compound of Prostaglandin E2(P838610). Prostaglandin E2 is the most common and biologically potent of mammalian prostaglandins. Oxytocic; abortifacient.

Technology Process of 15-epi-Prostaglandin E2

There total 40 articles about 15-epi-Prostaglandin E2 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:

(5Z,8R,9R,11S,12S,13E,15R)-11,15-bis-(tert-butyldimethylsilyloxy)-9-oxoprosta-5,13-dienoic acid (303015-41-0) → ent-prostaglandin E2 (363-24-6,13164-28-8,22230-04-2,27415-25-4,31660-13-6,31660-17-0,36150-00-2,37495-69-5,37785-90-3,38310-90-6,38873-82-4,39265-67-3,39648-42-5,54324-09-3,54324-10-6,57759-80-5,57759-81-6,63179-97-5,65026-02-0,65085-69-0,70051-84-2,85548-91-0) + ent-15-E2t-isoprostane

Guidance literature:

(5Z,8R,9R,11S,12S,13E,15R)-11,15-bis-(tert-butyldimethylsilyloxy)-9-oxoprosta-5,13-dienoic acid; With pyridine; hydrogen fluoride; In tetrahydrofuran; water; acetonitrile; at 20 ℃; for 6h;

With potassium acetate; In methanol; at 20 ℃; for 96h;

DOI:10.1016/S0040-4020(00)00531-7

Reference yield:

(Z)-7-[(1R,2S,3S,5R)-5-Acetoxy-3-hydroxy-2-((E)-(R)-3-hydroxy-oct-1-enyl)-cyclopentyl]-hept-5-enoic acid ethyl ester (214748-78-4) → ent-prostaglandin E2 (363-24-6,13164-28-8,22230-04-2,27415-25-4,31660-13-6,31660-17-0,36150-00-2,37495-69-5,37785-90-3,38310-90-6,38873-82-4,39265-67-3,39648-42-5,54324-09-3,54324-10-6,57759-80-5,57759-81-6,63179-97-5,65026-02-0,65085-69-0,70051-84-2,85548-91-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 82 percent / imidazole; DMAP / CH₂Cl₂ / 24 h / 20 °C

2.1: 92 percent / LiOH*H₂O / tetrahydrofuran; H₂O; methanol / 24 h / 20 °C

3.1: 95 percent / Dess-Martin periodinate / CH₂Cl₂ / 20 h / 20 °C

4.1: HF; pyridine / H₂O; tetrahydrofuran; acetonitrile / 6 h / 20 °C

4.2: KOAc / methanol / 96 h / 20 °C

With pyridine; 1H-imidazole; dmap; lithium hydroxide; hydrogen fluoride; Dess-Martin periodane; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; 1.1: Substitution / 2.1: Hydrolysis / 3.1: Oxidation / 4.1: Hydrolysis / 4.2: Isomerization;

DOI:10.1016/S0040-4020(00)00531-7

Reference yield:

(5Z,8R,9R,11S,12S,13E,15R)-11,15-bis-(tert-butyldimethylsilyloxy)-9-hydroxyprosta-5,13-dienoic acid (303015-43-2) → ent-prostaglandin E2 (363-24-6,13164-28-8,22230-04-2,27415-25-4,31660-13-6,31660-17-0,36150-00-2,37495-69-5,37785-90-3,38310-90-6,38873-82-4,39265-67-3,39648-42-5,54324-09-3,54324-10-6,57759-80-5,57759-81-6,63179-97-5,65026-02-0,65085-69-0,70051-84-2,85548-91-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / Dess-Martin periodinate / CH₂Cl₂ / 20 h / 20 °C

2.1: HF; pyridine / H₂O; tetrahydrofuran; acetonitrile / 6 h / 20 °C

2.2: KOAc / methanol / 96 h / 20 °C

With pyridine; hydrogen fluoride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1.1: Oxidation / 2.1: Hydrolysis / 2.2: Isomerization;

DOI:10.1016/S0040-4020(00)00531-7

upstream raw materials:

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

dimethyl 2-oxoheptylphosphonate

(4-carboxybutyl)triphenylphosphonium bromide

[3aR,4R(1E,3R),5R,6aS]-5-benzoyloxy-4-(3-hydroxyocten-1-yl)-hexahydro-2H-cyclopenta[b]furan-2-one

Downstream raw materials:

(+/-)-prostaglandin E₂ methyl ester