9S,11R-dihydroxy-15-oxo-5Z-prostaenoic acid-cyclo[8S,12R]

Base Information

• Chemical Name: 9S,11R-dihydroxy-15-oxo-5Z-prostaenoic acid-cyclo[8S,12R]
• CAS No.: 191919-02-5
• Molecular Formula: C₂₀H₃₄O₅
• Molecular Weight: 354.487
• DSSTox Substance ID: DTXSID80865371
• Nikkaji Number: J948.712C
• Metabolomics Workbench ID: 2820
• Mol file: 191919-02-5.mol

Synonyms:191919-02-5;9S,11R-dihydroxy-15-oxo-5Z-prostaenoic acid-cyclo[8S,12R];(Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-(3-oxooctyl)cyclopentyl]hept-5-enoic acid;8-iso-13,14-dihydro-15-keto-PGF2alpha;8-iso-13,14-dihydro-15-keto Prostaglandin F2alpha;Prost-5-en-1-oic acid, 9,11-dihydroxy-15-oxo-, (5Z,8beta,9alpha,11alpha)-;9alpha,11alpha-Dihydroxy-15-oxo-(8beta)-prost-5Z-en-1-oic acid;DTXSID80865371;LMFA03110004;8-iso-13,14-dihydro-15-keto-PGF2a;PD021316;9S,11R-dihydroxy-15-oxo-5Z-prostaenoate;9S,11R-dihydroxy-15-oxo-5Z-prostaenoic acid;SR-01000946855;J-012408;SR-01000946855-1;8-iso-13,14-dihydro-15-keto Prostaglandin F2 alpha;(5Z,8b,9a,11a)-9,11-dihydroxy-15-oxo-Prost-5-en-1-oate;(5Z)-9alpha,11alpha-Dihydroxy-15-oxo-8beta-prost-5-en-1-oic acid;(5Z,8b,9a,11a)-9,11-dihydroxy-15-oxo-Prost-5-en-1-oic acid

Chemical Property of 9S,11R-dihydroxy-15-oxo-5Z-prostaenoic acid-cyclo[8S,12R]

Chemical Property:

• Vapor Pressure: 4.72E-14mmHg at 25°C
• Boiling Point: 543°C at 760 mmHg
• Flash Point: 296.2°C
• PSA: 94.83000
• Density: 1.091g/cm³
• LogP: 3.47510
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 13
• Exact Mass: 354.24062418
• Heavy Atom Count: 25
• Complexity: 432

Purity/Quality:

97% ^*data from raw suppliers

8-iso-13,14-dihydro-15-keto Prostaglandin F2α ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(=O)CCC1C(CC(C1CC=CCCCC(=O)O)O)O
• Isomeric SMILES: CCCCCC(=O)CC[C@H]1[C@@H](C[C@@H]([C@H]1C/C=C\CCCC(=O)O)O)O

Technology Process of 9S,11R-dihydroxy-15-oxo-5Z-prostaenoic acid-cyclo[8S,12R]

There total 19 articles about 9S,11R-dihydroxy-15-oxo-5Z-prostaenoic acid-cyclo[8S,12R] 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: 59.0%

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) + 1-((3aR,5R,6aS)-2,5-Dihydroxy-hexahydro-cyclopenta[b]furan-4-yl)-octan-3-one (125010-78-8) → 15-oxo-13,14-dihydro-prostaglandin F2α (27376-76-7,67837-85-8,107615-77-0,191919-02-5)

Guidance literature:

With t-BuPK; In tetrahydrofuran; for 1h; Ambient temperature;

Reference yield:

(Z)-7-[(1R,2R,3S,5S)-3,5-Diacetoxy-2-(3-oxo-octyl)-cyclopentyl]-hept-5-enoic acid methyl ester (122220-99-9) → 9α-11β-dihydroxy-15-oxo-Z-prost-5-ene-1-oic acid (107615-77-0,191919-02-5)

Guidance literature:

With lithium hydroxide; In 1,2-dimethoxyethane; at 60 ℃; for 1h;

Reference yield:

[1,1'-bisphenyl]-4-carboxylic acid (3aR,4R,5R,6aS)-hexahydro-2-oxo-4-[(1E)-3-oxo-1-octen-1-yl]-2H-cyclopenta[b]furan-5-yl ester (31753-00-1) → 9α-11β-dihydroxy-15-oxo-Z-prost-5-ene-1-oic acid (107615-77-0,191919-02-5)

Guidance literature:

Multi-step reaction with 13 steps

1: 99 percent / H₂ / Pd/C / ethyl acetate / 4 h

2: 82 percent / zinc triflate / CH₂Cl₂ / 2 h / Ambient temperature

3: 89 percent / methanolic t-BuOK / methyl acetate / 2 h / Ambient temperature

4: 80 percent / p-toluenesulfonic acid / CH₂Cl₂ / 1 h / Ambient temperature

5: 94 percent / DIBAL / tetrahydrofuran / 0.5 h / -78 °C

6: 1.) lithium bis(trimethylsilyl)amide, HMPA / 1.) THF, 0 deg C, 30 min, 2.) THF, -40 -> 0 deg C, 30 min

8: 80 percent / CH₂Cl₂ / 0.5 h / 0 °C

9: 88 percent / cation exchange resin AG₅₀-X₈ / methanol / 6 h / 23 °C

10: triethylamine / CH₂Cl₂ / 0.5 h / -20 °C

11: 18-crown-6-ether / toluene / 8 h / 115 °C

12: 71 percent / aq. ceric ammonium nitrate / acetonitrile / 1 h / Ambient temperature

13: aq. LiOH / 1,2-dimethoxy-ethane / 1 h / 60 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium hydroxide; ammonium cerium(IV) nitrate; 18-crown-6 ether; cation exchange resin AG₅₀-X₈; potassium tert-butylate; hydrogen; zinc trifluoromethanesulfonate; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; acetic acid methyl ester; ethyl acetate; toluene; acetonitrile;

upstream raw materials:

(4-carboxybutyl)triphenylphosphonium bromide

1-((3aR,5R,6aS)-2,5-Dihydroxy-hexahydro-cyclopenta[b]furan-4-yl)-octan-3-one

1,2-epoxyheptane

4β-(3ξ-hydroxy-octan-1-yl)-5α-(t-butyldimethylsilyloxy)-2ξ-methoxy-3,3aβ,4,5,6,6aβ-hexahydro-2H-cyclopenta/b/furan

Downstream raw materials:

13,14-dihydro-15-keto prostaglandin E1