(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid

Base Information

• Chemical Name: (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid
• CAS No.: 37658-84-7
• Molecular Formula: C₂₀H₃₄O₅
• Molecular Weight: 354.487
• UNII: GB83QL2WR2
• DSSTox Substance ID: DTXSID301347941
• Nikkaji Number: J1.068.162F
• Wikidata: Q106039044
• Metabolomics Workbench ID: 2405
• Mol file: 37658-84-7.mol

Synonyms:15(R)-Prostaglandin F2alpha;37658-84-7;15-epi-PGF2alpha;15R-PGF2alpha;GB83QL2WR2;15beta-Pgf2alpha;(Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid;(15R)-Pgf2alpha;UNII-GB83QL2WR2;15R-Prostaglandin F2alpha;15-Epiprostaglandin F2alpha;15-epi-Prostaglandin F2alpha;8,15-diepi-15-F2t-IsoP;Dinoprost trometamol impurity B [EP];(5Z,9alpha,11alpha,13E,15R)-9,11,15-Trihydroxyprosta-5,13-dien-1-oic acid;9S,11R,15R-trihydroxy-5Z,13E-prostadienoic acid;Prosta-5,13-dien-1-oicacid, 9,11,15-trihydroxy-, (5Z,9a,11a,13E,15R)-;Emtricitabine dioxolane;15R PGF-2alpha;15-EPI-PGF2.ALPHA.;(15R)-PGF2.ALPHA.;15(R)-Prostaglandin F2.alpha.;15.BETA.-PGF2.ALPHA.;CHEBI:165306;DTXSID301347941;HMS3648F16;LMFA03010041;15-EPIPROSTAGLANDIN F2.ALPHA.;CS-O-13538;15-EPI-PROSTAGLANDIN F2.ALPHA.;PD021295;SR-01000946498;SR-01000946498-1;DINOPROST TROMETAMOL IMPURITY B [EP IMPURITY];(5Z,9.ALPHA.,11.ALPHA.,13E,15R)-9,11,15-TRIHYDROXYPROSTA-5,13-DIEN-1-OIC ACID;Prosta-5,13-dien-1-oic acid, 9,11,15-trihydroxy-, (5Z,9alpha,11alpha,13E,15R)-;PROSTA-5,13-DIEN-1-OIC ACID, 9,11,15-TRIHYDROXY-, (5Z,9.ALPHA.,11.ALPHA.,13E,15R)-

Chemical Property of (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid

Chemical Property:

• PSA: 97.99000
• LogP: 3.04290
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 12
• Exact Mass: 354.24062418
• Heavy Atom Count: 25
• Complexity: 432

Purity/Quality:

>99% ^*data from raw suppliers

15(R)-Prostaglandin F2α ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid

There total 85 articles about (Z)-7-[(1R,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic 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: 57.0%

C15H26O4 + (4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → prostaglandin F2α (551-11-1,4510-16-1,13164-29-9,23518-25-4,23518-26-5,27415-26-5,28977-22-2,36150-01-3,36150-02-4,37658-84-7,38310-95-1,38432-87-0,39762-37-3,42586-88-9,51262-67-0,51830-20-7,51830-21-8,52521-76-3,54324-23-1,54324-24-2,54324-25-3,54483-31-7,54483-32-8,57759-78-1,57759-79-2,57759-85-0,58717-39-8,59727-54-7,61046-31-9,61302-52-1,62446-65-5,64395-46-6,65026-00-8,65026-01-9,88391-39-3,88391-40-6,99880-86-1,117558-80-2,118456-51-2,123123-44-4,125411-82-7,146388-90-1)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1038/nature11411

Reference yield:

(3aR,6aS)-2-methoxy-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde → prostaglandin F2α (551-11-1,4510-16-1,13164-29-9,23518-25-4,23518-26-5,27415-26-5,28977-22-2,36150-01-3,36150-02-4,37658-84-7,38310-95-1,38432-87-0,39762-37-3,42586-88-9,51262-67-0,51830-20-7,51830-21-8,52521-76-3,54324-23-1,54324-24-2,54324-25-3,54483-31-7,54483-32-8,57759-78-1,57759-79-2,57759-85-0,58717-39-8,59727-54-7,61046-31-9,61302-52-1,62446-65-5,64395-46-6,65026-00-8,65026-01-9,88391-39-3,88391-40-6,99880-86-1,117558-80-2,118456-51-2,123123-44-4,125411-82-7,146388-90-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine / tetrahydrofuran

2.1: ozone / methanol; dichloromethane / -78 °C

2.2: -78 - 20 °C

3.1: hydrogenchloride / tetrahydrofuran; water / 16 h / 20 °C

4.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C

With hydrogenchloride; potassium tert-butylate; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1038/nature11411

Reference yield:

(3aR,6aS)-2-hydroxy-3,3a,6,6a-tetrahydro-2H-cyclopenta[b]furan-5-carbaldehyde → prostaglandin F2α (551-11-1,4510-16-1,13164-29-9,23518-25-4,23518-26-5,27415-26-5,28977-22-2,36150-01-3,36150-02-4,37658-84-7,38310-95-1,38432-87-0,39762-37-3,42586-88-9,51262-67-0,51830-20-7,51830-21-8,52521-76-3,54324-23-1,54324-24-2,54324-25-3,54483-31-7,54483-32-8,57759-78-1,57759-79-2,57759-85-0,58717-39-8,59727-54-7,61046-31-9,61302-52-1,62446-65-5,64395-46-6,65026-00-8,65026-01-9,88391-39-3,88391-40-6,99880-86-1,117558-80-2,118456-51-2,123123-44-4,125411-82-7,146388-90-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: magnesium sulfate / dichloromethane / 14 h / 20 °C

2.1: triethylamine / tetrahydrofuran

3.1: ozone / methanol; dichloromethane / -78 °C

3.2: -78 - 20 °C

4.1: hydrogenchloride / tetrahydrofuran; water / 16 h / 20 °C

5.1: potassium tert-butylate / tetrahydrofuran / 0 - 20 °C

With hydrogenchloride; potassium tert-butylate; magnesium sulfate; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water;

DOI:10.1038/nature11411

upstream raw materials:

(3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol

(4-carboxybutyl)triphenylphosphonium bromide

C₄₉H₅₄O₈

(1S,4R)-4-hydroxy-2-cyclopentenyl acetate