2,3-dinor-6,15-diketo-13,14-dihydroprostaglandin F1alpha

Base Information

• Chemical Name: 2,3-dinor-6,15-diketo-13,14-dihydroprostaglandin F1alpha
• CAS No.: 68376-88-5
• Molecular Formula: C18H30O6
• Molecular Weight: 342.43
• Mol file: 68376-88-5.mol

Synonyms:

Chemical Property of 2,3-dinor-6,15-diketo-13,14-dihydroprostaglandin F1alpha

Chemical Property:

• Vapor Pressure: 1.76E-14mmHg at 25°C
• Boiling Point: 551.9°C at 760 mmHg
• Flash Point: 301.6°C
• PSA: 111.90000
• Density: 1.159g/cm³
• LogP: 2.09790

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2,3-dinor-6,15-diketo-13,14-dihydroprostaglandin F1alpha

There total 13 articles about 2,3-dinor-6,15-diketo-13,14-dihydroprostaglandin F1alpha 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:

2,3-dinor-6-oxo-PGF(1α), 6.9-hemiacetal, 1,6-lactone → 5-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-oxo-octyl)-cyclopentyl]-4-oxo-pentanoic acid (68376-88-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: water; acetic acid / tetrahydrofuran / 60 h / 45 °C

2.1: Jones reagent / acetone / 1 h / -78 °C

2.2: -78 - 20 °C

3.1: platinum(IV) oxide; hydrogen / 25 °C

4.1: acetic acid / water

With platinum(IV) oxide; Jones reagent; water; hydrogen; acetic acid; In tetrahydrofuran; water; acetone;

Reference yield:

(1S,2R,3R,4R)-2-((Z)-5-Hydroxy-pent-2-enyl)-4-(tetrahydro-pyran-2-yloxy)-3-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentanol (82290-18-4) → 5-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-oxo-octyl)-cyclopentyl]-4-oxo-pentanoic acid (68376-88-5)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / -78 - -15 °C

2.1: sodium hydrogencarbonate; iodine / dichloromethane / 0.95 h / 5 - 10 °C

3.1: DBN / benzene / 20 h / 45 °C / Inert atmosphere

4.1: potassium hydrogensulfate / diethyl ether / 4.5 h / 20 °C

5.1: dmap; pyridine / 1.5 h / 20 °C

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5.5 h / 20 °C / Inert atmosphere

7.1: Jones reagent / acetone / 1 h / -30 - -16 °C

7.2: 0.05 h / 20 °C

7.3: 3.5 h / 45 °C

8.1: sodium hydroxide / water; tert-butyl alcohol / 1.5 h / 20 °C

9.1: Jones reagent / acetone / 1 h / -78 °C

9.2: -78 - 20 °C

10.1: platinum(IV) oxide; hydrogen / 25 °C

11.1: acetic acid / water

With pyridine; 1H-imidazole; dmap; platinum(IV) oxide; potassium hydrogensulfate; Jones reagent; DBN; tetrabutyl ammonium fluoride; hydrogen; iodine; sodium hydrogencarbonate; acetic acid; sodium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene;

Reference yield:

C34H61IO6Si → 5-[(1R,2R,3R,5S)-3,5-Dihydroxy-2-(3-oxo-octyl)-cyclopentyl]-4-oxo-pentanoic acid (68376-88-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: DBN / benzene / 20 h / 45 °C / Inert atmosphere

2.1: potassium hydrogensulfate / diethyl ether / 4.5 h / 20 °C

3.1: dmap; pyridine / 1.5 h / 20 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 5.5 h / 20 °C / Inert atmosphere

5.1: Jones reagent / acetone / 1 h / -30 - -16 °C

5.2: 0.05 h / 20 °C

5.3: 3.5 h / 45 °C

6.1: sodium hydroxide / water; tert-butyl alcohol / 1.5 h / 20 °C

7.1: Jones reagent / acetone / 1 h / -78 °C

7.2: -78 - 20 °C

8.1: platinum(IV) oxide; hydrogen / 25 °C

9.1: acetic acid / water

With pyridine; dmap; platinum(IV) oxide; potassium hydrogensulfate; Jones reagent; DBN; tetrabutyl ammonium fluoride; hydrogen; acetic acid; sodium hydroxide; In tetrahydrofuran; diethyl ether; water; acetone; tert-butyl alcohol; benzene;

upstream raw materials:

13,14-dihydro-2,3-dinor-6,15-dioxo-PGF₁α 6,9-hemiacetal 1,6-lactone

(1S,2R,3R,4R)-2-((Z)-5-Hydroxy-pent-2-enyl)-4-(tetrahydro-pyran-2-yloxy)-3-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentanol

Acetic acid (1S,2R,3R,4R)-2-[5-(tert-butyl-dimethyl-silanyloxy)-2-oxo-pentyl]-4-(tetrahydro-pyran-2-yloxy)-3-[(E)-(S)-3-(tetrahydro-pyran-2-yloxy)-oct-1-enyl]-cyclopentyl ester

2,3-dinor-6,15-dioxo-PGF₁α 6,9-hemiacetal 1,6-lactone

Refernces

• 1、 Bundy,Lin,Sih. "The synthesis of 2,3-dinorprostacyclin metabolites - A new approach to spirolactone hemiacetals". . p. 4419 - 4429. Retrieved 2014/12/11.