2,3-DINOR-11BETA-PROSTAGLANDIN F2ALPHA

Base Information

• Chemical Name: 2,3-DINOR-11BETA-PROSTAGLANDIN F2ALPHA
• CAS No.: 240405-20-3
• Molecular Formula: C₁₈H₃₀O₅
• Molecular Weight: 326.433
• Mol file: 240405-20-3.mol

Synonyms:3-Pentenoicacid, 5-[(1R,2R,3S,5S)-3,5-dihydroxy-2-[(1E,3S)-3-hydroxy-1-octenyl]cyclopentyl]-,(3Z)- (9CI)

Chemical Property of 2,3-DINOR-11BETA-PROSTAGLANDIN F2ALPHA

Chemical Property:

• PSA: 97.99000
• LogP: 2.26270

Purity/Quality:

99% ^*data from raw suppliers

2,3-dinor-11β-Prostaglandin F2α ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 2,3-dinor-11β-Prostaglandin F2α (2,3-dinor-11β-PGF2α) is a metabolite of PGD2 . Urinary excretion of 2,3-dinor-11β-PGF2α is increased in patients with mast cell activation disease (MCAD) and has been used as a marker of increased PGD2 levels. 2,3-dinor-11 β-PGF2α levels are also increased in the urine of patients with asthma and are positively correlated with impaired lung function.

Technology Process of 2,3-DINOR-11BETA-PROSTAGLANDIN F2ALPHA

There total 11 articles about 2,3-DINOR-11BETA-PROSTAGLANDIN F2ALPHA 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: 78.0%

(Z)-5-{(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-cyclopentyl}-pent-3-enoic acid (390746-28-8) → 2,3-dinor-iPF2α (240405-20-3)

Guidance literature:

With formic acid; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1016/S0040-4039(01)01794-4

Reference yield:

(4aS,5S,7R,7aS)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-hexahydro-cyclopenta[c]pyran-3-one (159697-96-8) → 2,3-dinor-iPF2α (240405-20-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 97 percent / DIBAL-H / CH₂Cl₂ / -78 °C

2: 85 percent / t-BuOK / tetrahydrofuran / 5 h / -20 °C

3: 97 percent / periodinane / CH₂Cl₂ / 2 h / 20 °C

4: 91 percent / LiHMDS / tetrahydrofuran / -78 °C

5: 96 percent / S-BINAL-H / tetrahydrofuran / 4 h / -100 °C

6: 99 percent / IM / CH₂Cl₂ / 8 h / 20 °C

7: 96 percent / Me₂AlCl / CH₂Cl₂ / 3 h / -20 - 20 °C

8: 97 percent / periodinane / 2-methyl-propan-2-ol; CH₂Cl₂ / 3 h / 20 °C

9: 96 percent / NaClO₂; 2-methyl-2-butene; KH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C

10: 78 percent / aq. formic acid / tetrahydrofuran / 3 h / 20 °C

With sodium chlorite; potassium dihydrogenphosphate; formic acid; 2-methyl-but-2-ene; (S)-BINAL-H; impramine; potassium tert-butylate; dimethylaluminum chloride; diisobutylaluminium hydride; Dess-Martin periodane; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;

DOI:10.1016/S0040-4039(01)01794-4

Reference yield:

(E)-(4S,6R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-6-((S)-2-thioxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid methyl ester (159697-94-6) → 2,3-dinor-iPF2α (240405-20-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 52 percent / n-Bu₃SnH; AIBN / benzene / 5 h / Heating

2: 97 percent / DIBAL-H / CH₂Cl₂ / -78 °C

3: 85 percent / t-BuOK / tetrahydrofuran / 5 h / -20 °C

4: 97 percent / periodinane / CH₂Cl₂ / 2 h / 20 °C

5: 91 percent / LiHMDS / tetrahydrofuran / -78 °C

6: 96 percent / S-BINAL-H / tetrahydrofuran / 4 h / -100 °C

7: 99 percent / IM / CH₂Cl₂ / 8 h / 20 °C

8: 96 percent / Me₂AlCl / CH₂Cl₂ / 3 h / -20 - 20 °C

9: 97 percent / periodinane / 2-methyl-propan-2-ol; CH₂Cl₂ / 3 h / 20 °C

10: 96 percent / NaClO₂; 2-methyl-2-butene; KH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 20 °C

11: 78 percent / aq. formic acid / tetrahydrofuran / 3 h / 20 °C

With sodium chlorite; potassium dihydrogenphosphate; formic acid; 2-methyl-but-2-ene; 2,2'-azobis(isobutyronitrile); (S)-BINAL-H; impramine; potassium tert-butylate; tri-n-butyl-tin hydride; dimethylaluminum chloride; diisobutylaluminium hydride; Dess-Martin periodane; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; benzene;

DOI:10.1016/S0040-4039(01)01794-4

upstream raw materials:

(Z)-5-{(1S,2R,3R,5S)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-dimethyl-silanyloxy)-oct-1-enyl]-cyclopentyl}-pent-3-enoic acid

(4aS,5S,7R,7aS)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-hexahydro-cyclopenta[c]pyran-3-one

(E)-(4S,6R)-4,6-Bis-(tert-butyl-dimethyl-silanyloxy)-6-((S)-2-thioxo-[1,3]dioxolan-4-yl)-hex-2-enoic acid methyl ester

(4aS,5S,7R,7aS)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-octahydro-cyclopenta[c]pyran-3-ol

Refernces