(E)-7-[3-hydroxy-2-[(E)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]-N-methylsulfonylhept-5-enamide

Base Information

• Chemical Name: (E)-7-[3-hydroxy-2-[(E)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]-N-methylsulfonylhept-5-enamide
• CAS No.: 60325-46-4
• Molecular Formula: C23H31 N O7 S
• Molecular Weight: 465.568
• European Community (EC) Number: 262-173-0
• Wikipedia: Sulprostone
• Mol file: 60325-46-4.mol

Synonyms:(E)-7-[3-hydroxy-2-[(E)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]-N-methylsulfonylhept-5-enamide;7-[(1R,2R,3R)-3-Hydroxy-2-[(3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]-N-methylsulfonylhept-5-enamide;60325-46-4;SCHEMBL94843;BDBM85183;NSC_43251;CAS_60325-46-4;(Z)-7-[(1R,2R,3R)-3-hydroxy-2-[(E,3R)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]-N-methylsulfonylhept-5-enamide

Chemical Property of (E)-7-[3-hydroxy-2-[(E)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]-N-methylsulfonylhept-5-enamide

Chemical Property:

• Appearance/Colour: white to off-white solid
• Melting Point: 78.5-80 ºC
• Refractive Index: 1.5650 (estimate)
• PSA: 138.38000
• Density: 1.3 g/cm³
• LogP: 3.21270
• Storage Temp.: −20°C
• Solubility.: DMSO: >5 mg/mL
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 465.18212350
• Heavy Atom Count: 32
• Complexity: 766

Purity/Quality:

98%,99%, ^*data from raw suppliers

Sulprostone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 60-36/37/38
• Safety Statements: 53-22-36/37-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CS(=O)(=O)NC(=O)CCCC=CCC1C(C(CC1=O)O)C=CC(COC2=CC=CC=C2)O
• Isomeric SMILES: CS(=O)(=O)NC(=O)CCC/C=C/CC1C(C(CC1=O)O)/C=C/C(COC2=CC=CC=C2)O
• Description: Sulprostone is a metabolism resistant synthetic analog of PGE2. It is a selective agonist for EP3 receptors with a Ki value of 0.35 nM at the human recombinant EP3-III receptor and an IC50 of 0.01 μM for the inhibition of PGE2 binding. Sulprostone is a potent stimulator of uterine smooth muscle contractions with high abortifacient activity.
• Uses: antimalarial activity Human chondrocytes3 and mouse adrenal chromaffin cells4 were treated with sulprostone to study the biological effects of PGE2. Sulprostone is a selective agonist of the PGE2 receptor.

Technology Process of (E)-7-[3-hydroxy-2-[(E)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]-N-methylsulfonylhept-5-enamide

There total 21 articles about (E)-7-[3-hydroxy-2-[(E)-3-hydroxy-4-phenoxybut-1-enyl]-5-oxocyclopentyl]-N-methylsulfonylhept-5-enamide 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%

N-{(Z)-7-[(1R,2R,3R)-5-Oxo-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoyl}-methanesulfonamide (64282-82-2) → Sulprostone (60325-46-4)

Guidance literature:

With acetic acid; for 14h;

DOI:10.1021/jm00143a018

Reference yield:

(3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-hexahydro-cyclopenta[b]furan-2-one (51638-93-8) → Sulprostone (60325-46-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.5 h

2: 79 percent / diisobutylaluminum hydride / toluene; hexane / 0.33 h

3: 1.) sodium methylsulfinylcarbanide / 1.) Me₂SO, 2.) Me₂SO, 2 h

4: Jones reagent / acetone / 0.08 h / -20 °C

5: 43 percent / 65percent aq. acetic acid / 14 h

With jones reagent; sodium methylsulfinylcarbanide; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; In hexane; dichloromethane; acetone; toluene;

DOI:10.1021/jm00143a018

Reference yield:

(3aR,4R,5R,6aS)-4-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol (286840-19-5) → Sulprostone (60325-46-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) sodium methylsulfinylcarbanide / 1.) Me₂SO, 2.) Me₂SO, 2 h

2: Jones reagent / acetone / 0.08 h / -20 °C

3: 43 percent / 65percent aq. acetic acid / 14 h

With jones reagent; sodium methylsulfinylcarbanide; acetic acid; In acetone;

DOI:10.1021/jm00143a018

upstream raw materials:

N-{(Z)-7-[(1R,2R,3R)-5-Oxo-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoyl}-methanesulfonamide

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

Corey aldehyde

7α-trimethylsilyloxy-6β-formyl-2-oxabicyclo<3.3.0>octan-3-one

Downstream raw materials:

N-(methanesulfonyl)-16-phenoxy-ω-tetranor-PGB₂-carboxamide

N-(methanesulfonyl)-16-phenoxy-ω-tetranor-PGA₂-carboxamide

Refernces

• 1、 Schaaf, Thomas K.,Bindra, Jasjit S.,Eggler, James F.,Plattner, Jacob J.,Nelson, A. James,et al.. "N-(Methanesulfonyl)-16-phenoxyprostaglandincarboxamides: Tissue-Selective, Uterine Stimulants". . p. 1353 - 1359. Retrieved 2007/10/02.