Gardrin

Base Information

• Chemical Name: Gardrin
• CAS No.: 73121-56-9
• Molecular Formula: C₂₃H₂₈O₆
• Molecular Weight: 400.472
• UNII: J4IP5Z9DAU
• Nikkaji Number: J2.200.785H,J2.200.786F,J32.841C
• Wikipedia: Enprostil
• NCI Thesaurus Code: C169951
• Metabolomics Workbench ID: 154602
• Mol file: 73121-56-9.mol

Synonyms:Enprostil;Enprostil, (1alpha(R*),2beta(1E,3R*),3alpha)-(+-)-Isomer;Enprostil, (1alpha(R*),2beta(1E,3S*),3alpha)-(+-)-Isomer;Enprostil, (1alpha,2alpha(1E,3S*),3beta)-(+-)-Isomer;Enprostil, (1alpha,2beta(1E,3R*),3alpha)-(+-)-Isomer;Enprostil, (1R-(1(R*),2beta(1E,3R*),3alpha))-Isomer;Enprostil, (1R-(1alpha(S*),2beta(1E,3R*),3alpha))-Isomer;Enprostil, (1R-(1alpha,2beta(1E,3R*),3alpha))-Isomer;Enprostil, (1S-(1alpha(R*),2beta(1E,3R*),3alpha))-Isomer;Enprostil, (1S-(1alpha(S*),2beta(1E,3R*),3alpha))-Isomer;Gardrin;RS 84135;RS-84135;RS84135

Chemical Property of Gardrin

Chemical Property:

• Vapor Pressure: 4.64E-13mmHg at 25°C
• Melting Point: <46 °C
• Boiling Point: 552.9°C at 760 mmHg
• PKA: 13.46±0.20(Predicted)
• Flash Point: 185.7°C
• PSA: 93.06000
• Density: 1.201g/cm³
• LogP: 2.60320
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly)
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 400.18858861
• Heavy Atom Count: 29
• Complexity: 613

Purity/Quality:

99% ^*data from raw suppliers

rac-Enprostil ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Moderately toxic by ingestion.
• Hazard Codes: Moderately toxic by ingestion.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCC=C=CCC1C(C(CC1=O)O)C=CC(COC2=CC=CC=C2)O
• Isomeric SMILES: COC(=O)CCC=C=CC[C@H]1[C@@H]([C@H](CC1=O)O)/C=C/[C@@H](COC2=CC=CC=C2)O
• Description: Enprostil is one of three, orally-active prostaglandins (see rnisoprostol and rosaprostol) for the treatment of gastric and duodenal ulcers. An allenic PGE2 derivative, enprostil is both antisecretory (acid, gastrin) and cytoprotective.
• Uses: Enprostil is a synthetic analogue of prostaglandin E2 and was found to be effective in the treatment of patients with duodenal or gastric ulcers. Antisecretory; antiulcerative.

Technology Process of Gardrin

There total 17 articles about Gardrin 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: 67.0%

methyl 11α,15α-bis(tetrahydropyran-2-yloxy)-16-phenoxy-9-oxo-17,18,19,20-tetranorprosta-4,5,13(E)-trienoate → (dl)-9-keto-11α,15α-dihydroxy-16-phenoxy-17,18,19,20-tetranorprosta-4,5,13-trans-trienoic acid methyl ester (73121-56-9,82444-04-0,93000-00-1,99631-10-4,99631-11-5,105368-46-5,105368-47-6,108815-43-6,108815-44-7,108815-47-0,108815-66-3,111408-96-9,111408-97-0,125638-68-8)

Guidance literature:

With water; acetic acid; In tetrahydrofuran; at 40 ℃; for 14h;

DOI:10.1055/s-1994-25576

Reference yield: 67.0%

(-)-11α,15α-bis<(tert-butyldimethylsilyl)oxy>-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester (157543-66-3) → (dl)-9-keto-11α,15α-dihydroxy-16-phenoxy-17,18,19,20-tetranorprosta-4,5,13-trans-trienoic acid methyl ester (73121-56-9,82444-04-0,93000-00-1,99631-10-4,99631-11-5,105368-46-5,105368-47-6,108815-43-6,108815-44-7,108815-47-0,108815-66-3,111408-96-9,111408-97-0,125638-68-8)

Guidance literature:

With pyridine; hydrogen fluoride; In acetonitrile; for 3h;

DOI:10.1021/jo00066a020

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) → (dl)-9-keto-11α,15α-dihydroxy-16-phenoxy-17,18,19,20-tetranorprosta-4,5,13-trans-trienoic acid methyl ester (73121-56-9,82444-04-0,93000-00-1,99631-10-4,99631-11-5,105368-46-5,105368-47-6,108815-43-6,108815-44-7,108815-47-0,108815-66-3,111408-96-9,111408-97-0,125638-68-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 91 percent / tetrahydrofuran / 5 h / Ambient temperature

2: 91 percent / Et₃N, DMAP / CH₂Cl₂ / 3 h / Ambient temperature

3: 76 percent / CuI*P(OEt)3 / tetrahydrofuran / -40 deg C then 0 deg C, 2 h

4: TBAF / tetrahydrofuran / 3 h / Ambient temperature

5: K₂CO₃ / methanol / 5 h / Ambient temperature

6: pyridinium dichromate / CH₂Cl₂ / 24 h / Ambient temperature

7: pyridinium dichromate / dimethylformamide / 24 h / Ambient temperature

8: 67 percent / AcOH, H₂O / tetrahydrofuran / 14 h / 40 °C

With dmap; dipyridinium dichromate; triethylphosphite copper(I) iodide complex; tetrabutyl ammonium fluoride; water; potassium carbonate; acetic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-1994-25576

upstream raw materials:

(-)-11α,15α-bis<(tert-butyldimethylsilyl)oxy>-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-4,15,13(t)-trienoic acid methyl ester

(3S,4R)-3-(Methoxymethyloxy)-2-methylidene-4-(tert-butyldimethylsiloxy)cyclopentanone

(R)-3-<(tert-butyldimethylsilyl)oxy>-4-phenoxy-1-butyne

(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

Refernces

• 1、 Lee,Nam,Jung,Park. "Synthesis of prostaglandins III: Efficient and practical synthesis of antisecretory prostaglandin enprostil". . p. 792 - 794. Retrieved 2007/10/02.
• 2、 Cooper,Wren,Jackson,Beard,Galeazzi,Van Horn,Li. "Synthesis of the four stereoisomers of enprostil". . p. 4280 - 4286. Retrieved 2007/10/02.