(Z)-7-[(1R,2R,3R,5S)-5-ACETOXY-3-HYDROXY-2-((E)-(S)-3-HYDROXY-OCT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER

Base Information

• Chemical Name: (Z)-7-[(1R,2R,3R,5S)-5-ACETOXY-3-HYDROXY-2-((E)-(S)-3-HYDROXY-OCT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER
• CAS No.: 55022-57-6
• Molecular Formula: C23H38O6
• Molecular Weight: 410.551
• Mol file: 55022-57-6.mol

Synonyms:(Z)-7-[(1R,2R,3R,5S)-5-ACETOXY-3-HYDROXY-2-((E)-(S)-3-HYDROXY-OCT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER;(Z)-7-[(1R,2R,3R,5S)-5-ACETOXY-3-HYDROXY-2-((E)-(S)-3-HYDROXY-OCT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER

Chemical Property of (Z)-7-[(1R,2R,3R,5S)-5-ACETOXY-3-HYDROXY-2-((E)-(S)-3-HYDROXY-OCT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER

Chemical Property:

• PSA: 93.06000
• LogP: 3.70210

Purity/Quality:

99%min ^*data from raw suppliers

(Z)-7-((1R,2R,3R,5S)-5-ACETOXY-3-HYDROXY-2-((E)-(S)-3-HYDROXY-OCT-1-ENYL)-CYCLOPENTYL)-HEPT-5-ENOIC ACID METHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (Z)-7-[(1R,2R,3R,5S)-5-ACETOXY-3-HYDROXY-2-((E)-(S)-3-HYDROXY-OCT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER

There total 35 articles about (Z)-7-[(1R,2R,3R,5S)-5-ACETOXY-3-HYDROXY-2-((E)-(S)-3-HYDROXY-OCT-1-ENYL)-CYCLOPENTYL]-HEPT-5-ENOIC ACID METHYL ESTER 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: 93.0%

methyl (5Z)-7-{(1R,2R,3R,5S)-5-acetoxy-2-[(1E,3S)-3-hydroxy-1-octenyl]-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate (55022-56-5) → methyl (5Z)-7-{(1R,2R,3R,5R)-5-acetoxy-3-hydroxy-2-[(1E,3S)-3-hydroxy-1-octenyl]cyclopentyl}-5-heptenoate (55022-57-6)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; at 40 ℃;

DOI:10.1055/s-1997-3268

Reference yield: 57.0%

(Z)-7-{(1R,2R,3R,5S)-5-Acetoxy-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-hept-5-enoic acid methyl ester (63521-06-2) → methyl (5Z)-7-{(1R,2R,3R,5R)-5-acetoxy-3-hydroxy-2-[(1E,3S)-3-hydroxy-1-octenyl]cyclopentyl}-5-heptenoate (55022-57-6)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; Ambient temperature;

DOI:10.1021/jo00146a019

Reference yield:

(2R,3S)-5-tert-butyldimethylsilyloxy-2,3-epoxypentan-1-ol (136235-73-9) → methyl (5Z)-7-{(1R,2R,3R,5R)-5-acetoxy-3-hydroxy-2-[(1E,3S)-3-hydroxy-1-octenyl]cyclopentyl}-5-heptenoate (55022-57-6)

Guidance literature:

Multi-step reaction with 24 steps

1.1: CuCN / tetrahydrofuran; diethyl ether / 1 h / -30 °C

1.2: tetrahydrofuran; diethyl ether / 8 h / -12 °C

2.1: pyridinium p-toluenesulfonate / CHCl₃ / 12 h / 20 °C

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: Ph₃P / CH₂Cl₂ / 12 h / 20 °C

4.1: benzene / 7 h / 65 °C

5.1: DIBAL-H / toluene; hexane / 1 h / -78 °C

6.1: PCC; NaOAc; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 0 °C

7.1: BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C

7.2: tetrahydrofuran; hexane / 3 h / -78 - 0 °C

8.1: tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

9.1: Dess-Martin reagent / CH₂Cl₂ / 1 h / 0 °C

10.1: Ni(cod)2; PPh₃; i-Bu₂-ALAC / toluene / 2 h / 0 °C

11.1: imidazole / dimethylformamide / 7 h / 20 °C

12.1: O₃; O₂ / CH₂Cl₂ / -78 °C

12.2: PPh₃ / CH₂Cl₂ / 12 h / 20 °C

13.1: potassium tert-butoxide / tetrahydrofuran / 1 h / 20 °C

13.2: tetrahydrofuran / 0.25 h

14.1: methanol; diethyl ether / 0 °C

15.1: tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 20 °C

16.1: DMAP; pyridine / CH₂Cl₂ / 2 h / 20 °C

17.1: Dowex₅₀^W / methanol / 0.5 h / 50 °C

18.1: Et₃N; DMAP / CH₂Cl₂ / 36 h / 20 °C

19.1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 12 h / 20 °C

20.1: tetrabutylammonium fluoride / tetrahydrofuran / 16 h / 0 °C

21.1: PCC; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 0 °C

22.1: NaH / tetrahydrofuran / 0.08 h / 20 °C

22.2: tetrahydrofuran / 1 h

23.1: LiAlH₄; (S)-binaphthol / tetrahydrofuran; ethanol / 1 h / -78 °C

24.1: aq. AcOH / tetrahydrofuran / 2.5 h / 40 °C

With pyridine; 1H-imidazole; dmap; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; lithium aluminium tetrahydride; n-butyllithium; diisobutylaluminium acetylacetonate; (S)-binaphthol; 4 A molecular sieve; Dowex₅₀^W; potassium tert-butylate; tetrabutyl ammonium fluoride; oxygen; sodium acetate; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; ozone; acetic acid; triethylamine; triphenylphosphine; pyridinium chlorochromate; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1248/cpb.48.1753

upstream raw materials:

(Z)-7-{(1R,2R,3R,5S)-5-Acetoxy-3-(tetrahydro-pyran-2-yloxy)-2-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl}-hept-5-enoic acid methyl ester

methyl (5Z)-7-{(1R,2R,3R,5S)-5-acetoxy-2-[(1E,3S)-3-hydroxy-1-octenyl]-3-[(2-oxacyclohexyl)oxy]-cyclopentyl}-5-heptenoate

(4-carboxybutyl)triphenylphosphonium bromide

(2R,3S)-5-tert-butyldimethylsilyloxy-2,3-epoxypentan-1-ol

Downstream raw materials:

(+)-prostaglandin F_2α

dinoprost

15-epi-PGF_2α

Refernces

• 1、 Sato,Takimoto,Mori. "Total synthesis of prostaglandin F(2α) using nickel-catalyzed stereoselective cyclization of 1,3-diene and tethered aldehyde via transmetalation of nickelacycle with diisobutylaluminum acetylacetonate". . p. 1753 - 1760. Retrieved 2007/10/03.