6,15-dioxo-9S,11R-dihydroxy-13E-prostenoic acid

Base Information

Chemical Name:6,15-dioxo-9S,11R-dihydroxy-13E-prostenoic acid
CAS No.:63446-59-3
Molecular Formula:C₂₀H₃₂O₆
Molecular Weight:368.47
Hs Code.:
Wikidata:Q27140003
Metabolomics Workbench ID:2383
Mol file:63446-59-3.mol

Synonyms:6,15-dioxo-9S,11R-dihydroxy-13E-prostenoic acid;63446-59-3;7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E)-3-oxooct-1-enyl]cyclopentyl]-6-oxoheptanoic acid;6,15-diketo,13,14-dihydroprostaglandin F1alpha;CHEBI:72595;6,15dk,13,14dh-PGF1a;6,15-diketo-13,14-dihydro-PGF1a;6,15-Diketo,13,14-dihydro-PGF1a;6,15-diketo,13,14-dihydro-PGF1alpha;6,15-dioxo-9S,11R-dihydroxy-13E-prostenoate;Q27140003;(9alpha,11alpha,13E)-9,11-dihydroxy-6,15-dioxoprost-13-en-1-oic acid

Suppliers and Price of 6,15-dioxo-9S,11R-dihydroxy-13E-prostenoic acid

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 6,15-dioxo-9S,11R-dihydroxy-13E-prostenoic acid

Chemical Property:

Vapor Pressure:6.99E-16mmHg at 25°C
Boiling Point:580.3°C at 760 mmHg
Flash Point:318.8°C
PSA：111.90000
Density:1.188g/cm³
LogP:2.65410
XLogP3:1.3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:13
Exact Mass:368.21988874
Heavy Atom Count:26
Complexity:499

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CCCCCC(=O)C=CC1C(CC(C1CC(=O)CCCCC(=O)O)O)O
Isomeric SMILES:CCCCCC(=O)/C=C/[C@H]1[C@@H](C[C@@H]([C@@H]1CC(=O)CCCCC(=O)O)O)O

Technology Process of 6,15-dioxo-9S,11R-dihydroxy-13E-prostenoic acid

There total 16 articles about 6,15-dioxo-9S,11R-dihydroxy-13E-prostenoic acid 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:

: triisopropylsilyl 7-((1R,2R,3R,5S)-3-(tertbutyldimethylsilyloxy)-2-((E)-3-oxooct-1-enyl)-5-(triethylsilyloxy)cyclopentyl)-6-oxoheptanoate

: 63446-59-3
7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((E)-3-oxooct-1-enyl)cyclopentyl)-6-oxoheptanoic acid

: C₂₀H₃₂O₆

Guidance literature:: With pyridine; pyridine hydrogenfluoride; In acetonitrile; at 20 ℃; for 14h; Overall yield = 99 percent; Overall yield = 15.5 mg; Inert atmosphere;
DOI:10.1016/j.tet.2019.130593

Reference yield:

: (2S,3R,4R)-4-(tert-butyldimethylsilyloxy)-2-(1-hydroxy-2-(triethylsilyloxy)ethyl)-3-vinylcyclopentanone

: 63446-59-3
7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((E)-3-oxooct-1-enyl)cyclopentyl)-6-oxoheptanoic acid

: C₂₀H₃₂O₆

Guidance literature:: Multi-step reaction with 13 steps

1: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere

2: pyridinium p-toluenesulfonate / methanol / 1.17 h / 0 °C / Inert atmosphere

3: sodium periodate / water; methanol / 0.5 h / 0 °C / Inert atmosphere

4: dmap; pyridine / 0.33 h / 20 °C / Inert atmosphere

5: sodium tetrahydroborate / methanol / 0.5 h / 0 °C / Inert atmosphere

6: triethylamine / dichloromethane / 0.25 h / -40 °C / Inert atmosphere

7: dimethyl sulfoxide / 28 h / 20 - 60 °C / Inert atmosphere

8: diisobutylaluminium hydride / cyclohexane; dichloromethane / 0.25 h / -78 °C / Inert atmosphere

9: chromium dichloride; nickel dichloride / dimethyl sulfoxide; tetrahydrofuran / 9 h / 20 °C / Inert atmosphere

10: Dess-Martin periodane / dichloromethane / 4 h / 0 °C / Inert atmosphere

11: (triphenylphosphine)copper(I) hydride hexamer; tert-butyl alcohol / toluene / 1 h / 20 °C / Inert atmosphere

12: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / dichloromethane / 11 h / Inert atmosphere; Reflux

13: pyridine; pyridine hydrogenfluoride / acetonitrile / 14 h / 20 °C / Inert atmosphere

With pyridine; chromium dichloride; dmap; sodium tetrahydroborate; sodium periodate; (triphenylphosphine)copper(I) hydride hexamer; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; nickel dichloride; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; cyclohexane; water; dimethyl sulfoxide; toluene; acetonitrile; 9: |Nozaki-Hiyama-Kishi Reaction / 12: |Cross Metathesis;
DOI:10.1016/j.tet.2019.130593

Reference yield:

: ((1S,2R,3R,5S)-3-(tert-butyldimethylsilyloxy)-5-(triethylsilyloxy)-2-vinylcyclopentyl)methanol

: 63446-59-3
7-((1R,2R,3R,5S)-3,5-dihydroxy-2-((E)-3-oxooct-1-enyl)cyclopentyl)-6-oxoheptanoic acid

: C₂₀H₃₂O₆

Guidance literature:: Multi-step reaction with 8 steps

1: triethylamine / dichloromethane / 0.25 h / -40 °C / Inert atmosphere

2: dimethyl sulfoxide / 28 h / 20 - 60 °C / Inert atmosphere

3: diisobutylaluminium hydride / cyclohexane; dichloromethane / 0.25 h / -78 °C / Inert atmosphere

4: chromium dichloride; nickel dichloride / dimethyl sulfoxide; tetrahydrofuran / 9 h / 20 °C / Inert atmosphere

5: Dess-Martin periodane / dichloromethane / 4 h / 0 °C / Inert atmosphere

6: (triphenylphosphine)copper(I) hydride hexamer; tert-butyl alcohol / toluene / 1 h / 20 °C / Inert atmosphere

7: 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride / dichloromethane / 11 h / Inert atmosphere; Reflux

8: pyridine; pyridine hydrogenfluoride / acetonitrile / 14 h / 20 °C / Inert atmosphere

With pyridine; chromium dichloride; (triphenylphosphine)copper(I) hydride hexamer; 1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene[2-(iso-propoxy)-5-(N,N-dimethylaminosulfonyl)phenyl]methylene ruthenium(II) dichloride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; nickel dichloride; tert-butyl alcohol; In tetrahydrofuran; dichloromethane; cyclohexane; dimethyl sulfoxide; toluene; acetonitrile; 4: |Nozaki-Hiyama-Kishi Reaction / 7: |Cross Metathesis;
DOI:10.1016/j.tet.2019.130593