11-DEOXY-11-METHYLENE PROSTAGLANDIN D2

Base Information

• Chemical Name: 11-DEOXY-11-METHYLENE PROSTAGLANDIN D2
• CAS No.: 100648-29-1
• Molecular Formula: C₂₁H₃₄O₄
• Molecular Weight: 350.499
• Mol file: 100648-29-1.mol

Synonyms:11-Deoxy-11-methylene-PGD2

Chemical Property of 11-DEOXY-11-METHYLENE PROSTAGLANDIN D2

Chemical Property:

• PSA: 77.76000
• LogP: 4.23820

Purity/Quality:

99% ^*data from raw suppliers

11-deoxy-11-methylene Prostaglandin D2 ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Prostaglandin D2 (PGD2; ) is one of the five primary enzymatic prostaglandins derived directly from PGH2 . PGD2 is produced abundantly in the CSF by the lipocalin-type PGD synthase, and in the periphery by myeloid cells including mast cells and basophils by a second, leukocyte-type PGD synthase. 11-deoxy-11-methylene PGD2 is a novel, chemically stable, isosteric analog of PGD2 wherein the 11-keto group is replaced by an exocyclic methylene. In the PGE series, the analogous modification leads to a stable, somewhat less potent agonist which embodies the same uterine stimulant and cervical ripening activities as the parent prostaglandin. However, 11-deoxy-11-methylene PGD2 has been reported by one group to be essentially without agonist activity on human platelets, a DP1 receptor assay.

Technology Process of 11-DEOXY-11-METHYLENE PROSTAGLANDIN D2

There total 8 articles about 11-DEOXY-11-METHYLENE PROSTAGLANDIN D2 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: 60.0%

(Z)-7-[(1R,2R,5S)-5-Hydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-3-methylene-cyclopentyl]-hept-5-enoic acid methyl ester (104329-86-4) → 11-deoxo-11-methylene-prostaglandine D2 (100648-29-1)

Guidance literature:

With potassium hydroxide; In methanol; water;

DOI:10.1248/cpb.33.4625

Reference yield:

(4-carboxybutyl)triphenylphosphonium bromide (17814-85-6) → 11-deoxo-11-methylene-prostaglandine D2 (100648-29-1)

Guidance literature:

Multi-step reaction with 7 steps

2: 92 percent / imidazole / dimethylformamide

3: 78 percent / acetic acid / H₂O; tetrahydrofuran / 70 °C

4: 97.5 percent / PCC

5: 54.8 percent / Zn, TiCl₄ / CH₂Cl₂ / Ambient temperature

6: 68 percent / _nBu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 25 °C

7: 60 percent / KOH / methanol; H₂O

With 1H-imidazole; potassium hydroxide; tetrabutyl ammonium fluoride; titanium tetrachloride; acetic acid; pyridinium chlorochromate; zinc; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.33.4625

Reference yield:

(3aR,4R,5R,6aS)-4-[(E)-(S)-3-(tert-Butyl-diphenyl-silanyloxy)-oct-1-enyl]-5-(tetrahydro-furan-2-yloxy)-hexahydro-cyclopenta[b]furan-2-one → 11-deoxo-11-methylene-prostaglandine D2 (100648-29-1)

Guidance literature:

Multi-step reaction with 7 steps

2: 92 percent / imidazole / dimethylformamide

3: 78 percent / acetic acid / H₂O; tetrahydrofuran / 70 °C

4: 97.5 percent / PCC

5: 54.8 percent / Zn, TiCl₄ / CH₂Cl₂ / Ambient temperature

6: 68 percent / _nBu₄N⁽¹⁺⁾*F^(1-) / tetrahydrofuran / 25 °C

7: 60 percent / KOH / methanol; H₂O

With 1H-imidazole; potassium hydroxide; tetrabutyl ammonium fluoride; titanium tetrachloride; acetic acid; pyridinium chlorochromate; zinc; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1248/cpb.33.4625

upstream raw materials:

(Z)-7-[(1R,2R,5S)-5-Hydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-3-methylene-cyclopentyl]-hept-5-enoic acid methyl ester

(4-carboxybutyl)triphenylphosphonium bromide

(Z)-7-{(1R,2R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-3-methylene-cyclopentyl}-hept-5-enoic acid methyl ester

(Z)-7-{(1R,2R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-2-[(E)-(S)-3-(tert-butyl-diphenyl-silanyloxy)-oct-1-enyl]-3-oxo-cyclopentyl}-hept-5-enoic acid methyl ester

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