(E,6S)-8-[(1R,2R,3S,5R)-2-[(Z)-hept-2-enyl]-3,5-dihydroxycyclopentyl]-6-hydroxyoct-7-enoic acid

Base Information

• Chemical Name: (E,6S)-8-[(1R,2R,3S,5R)-2-[(Z)-hept-2-enyl]-3,5-dihydroxycyclopentyl]-6-hydroxyoct-7-enoic acid
• CAS No.: 152561-64-3
• Molecular Formula: C₂₀H₃₄O₅
• Molecular Weight: 354.487
• Wikidata: Q76389342
• Mol file: 152561-64-3.mol

Synonyms:152561-64-3;(5Z,9-alpha,11-alpha,13E,15S)-9,11,15-Trihydroxyprost-5,13-dien-20-oic acid;(+)-1-Decarboxy-1-methyl-20-nor-19-carboxyprostaglandin F(sub 2-alpha);Prost-5,13-dien-20-oic acid, 9,11,15-trihydroxy-, (5Z,9-alpha,11-alpha,13E,15S)-;(E,6S)-8-[(1R,2R,3S,5R)-2-[(Z)-hept-2-enyl]-3,5-dihydroxycyclopentyl]-6-hydroxyoct-7-enoic acid;LS-125851

Chemical Property of (E,6S)-8-[(1R,2R,3S,5R)-2-[(Z)-hept-2-enyl]-3,5-dihydroxycyclopentyl]-6-hydroxyoct-7-enoic acid

Chemical Property:

• Vapor Pressure: 1.8E-13mmHg at 25°C
• Boiling Point: 530.6°Cat760mmHg
• Flash Point: 288.7°C
• PSA: 0.00000
• Density: 1.153g/cm³
• LogP: 0.00000
• 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%min ^*data from raw suppliers

(+)-1-DECARBOXY-1-METHYL-20-NOR-19-CARBOXYPROSTAGLANDIN F(SUB 2-ALPHA) 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCC=CCC1C(CC(C1C=CC(CCCCC(=O)O)O)O)O
• Isomeric SMILES: CCCC/C=C\C[C@H]1[C@H](C[C@H]([C@@H]1/C=C/[C@H](CCCCC(=O)O)O)O)O

Technology Process of (E,6S)-8-[(1R,2R,3S,5R)-2-[(Z)-hept-2-enyl]-3,5-dihydroxycyclopentyl]-6-hydroxyoct-7-enoic acid

There total 22 articles about (E,6S)-8-[(1R,2R,3S,5R)-2-[(Z)-hept-2-enyl]-3,5-dihydroxycyclopentyl]-6-hydroxyoct-7-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: 43.0%

(+)-3α-(2Z-heptenyl)-2β-(3α,β-hydroxy-7-ethoxycarbonyl-2E-heptenyl)-1α,4α-dibenzoyloxycyclopentane → (+)-1-decarboxy-1-methyl-20-nor-19-carboxyprostaglandin F2α (152561-64-3) + (+)-1-Decarboxy-1-methyl-20-nor-19-carboxyprostaglandin F2α (152561-64-3)

Guidance literature:

With potassium hydroxide; In methanol; water; for 48h; Ambient temperature;

Reference yield: 43.0%

(+)-3α-(2Z-heptenyl)-2β-(3α,β-hydroxy-7-ethoxycarbonyl-2E-heptenyl)-1α,4α-dibenzoyloxycyclopentane → (+)-1-decarboxy-1-methyl-20-nor-19-carboxyprostaglandin F2α (152561-64-3) + (+)-1-Decarboxy-1-methyl-20-nor-19-carboxyprostaglandin F2α (152561-64-3)

Guidance literature:

With potassium hydroxide; In methanol; water; for 48h; Ambient temperature;

Reference yield:

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one (32233-40-2) → (+)-1-decarboxy-1-methyl-20-nor-19-carboxyprostaglandin F2α (152561-64-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 87 percent / pyridine / 48 h / 20 °C

2: diisobutylaluminnum hydride / CH₂Cl₂; hexane / 1 h / -78 °C

3: 1.) hexamethyldisilylazide / 1.) benzene, 75 deg C, 30 min, 2.) benzene, RT, 3 h

4: pyridine / 0.75 h

5: aq. AcOH / tetrahydrofuran / 2 h / Heating

6: 1.8 g / chromic anhydride, pyridine / CH₂Cl₂ / 0.25 h / 0 °C

7: triethylbenzylammonium chloride, 50percent aq. NaOH / CH₂Cl₂ / 0.33 h / Ambient temperature

8: 95 percent / NaBH₄ / ethanol / 0.5 h / 0 °C

9: 42 percent / KOH / methanol; H₂O / 48 h / Ambient temperature

With pyridine; chromium(VI) oxide; potassium hydroxide; sodium hydroxide; sodium tetrahydroborate; N-benzyl-N,N,N-triethylammonium chloride; hexamethyldisilazide; diisobutylaluminium hydride; acetic acid; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water;

upstream raw materials:

(3aR,4S,5R,6aS)-5-hydroxy-4-(hydroxymethyl)hexahydro-2H-cyclopenta[b]furan-2-one

diethyl adipate

(-)-7α-hydroxy-6β-triphenylmethoxymethyl-cis-2-oxabicyclo<3.3.0>octan-3-one

2-oxo-6-(ethoxycarbonyl)hexylphosphonic acid dimethyl ester

Refernces

• 1、 Tolstikov, G. A.,Akhmetvaleev, R. R.,Zhurba, V. M.,Miftakhov, M. S.. "PROSTANOIDS. LIV. ALTERNATIVES TO NATURAL PROSTAGLANDINS". . p. 1491 - 1496. Retrieved 2007/10/02.