Limaprost alfadex

Base Information

• Chemical Name: Limaprost alfadex
• CAS No.: 88852-12-4
• Deprecated CAS: 114868-77-8
• Molecular Formula: C57H94O35
• Molecular Weight: 1353.36
• European Community (EC) Number: 832-042-8
• Mol file: 88852-12-4.mol

Synonyms:limaprost-alfadex;limaprost-alpha-cyclodextrin complex;Opalmon

Chemical Property of Limaprost alfadex

Chemical Property:

• PSA: 569.73000
• LogP: -9.16760
• Hydrogen Bond Donor Count: 21
• Hydrogen Bond Acceptor Count: 35
• Rotatable Bond Count: 18
• Exact Mass: 1338.5575647
• Heavy Atom Count: 92
• Complexity: 1740

Purity/Quality:

98% ^*data from raw suppliers

LIMAPROST ALFADEX 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCC(C)CC(C=CC1C(CC(=O)C1CCCC=CC(=O)O)O)O.C(C1C2C(C(C(O1)OC3C(OC(C(C3O)O)OC4C(OC(C(C4O)O)OC5C(OC(C(C5O)O)OC6C(OC(C(C6O)O)OC7C(OC(O2)C(C7O)O)CO)CO)CO)CO)CO)O)O)O
• Isomeric SMILES: CCCC[C@H](C)C[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCC/C=C\C(=O)O)O)O.C([C@@H]1[C@@H]2[C@@H]([C@H]([C@H](O1)O[C@@H]3[C@H](O[C@@H]([C@@H]([C@H]3O)O)O[C@@H]4[C@H](O[C@@H]([C@@H]([C@H]4O)O)O[C@@H]5[C@H](O[C@@H]([C@@H]([C@H]5O)O)O[C@@H]6[C@H](O[C@@H]([C@@H]([C@H]6O)O)O[C@@H]7[C@H](O[C@H](O2)[C@@H]([C@H]7O)O)CO)CO)CO)CO)CO)O)O)O
• Recent NIPH Clinical Trials: Clinical effect of NTN tablets on lumbar spinal canal stenosis with low back pain
• Description: Limaprost is an orally-active antithrombotic and vasodilator structurally related to alprostadil. Oral administration of limaprost causes a dose-dependent inhibition of platelet aggregation, an increase in platelet CAMP and a mild suppression of platelet adhesiveness. In patients with pulmonary emphysema, tuberculosis, and chronic lung disease, treatment with limaprost reportedly produces significant cardiac improvements.
• Uses: Limaprost Alfadex is used in the sysnthesis of prostaglandins and its derivatives.

Technology Process of Limaprost alfadex

There total 28 articles about Limaprost alfadex 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: 73.0%

(E)-7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(3S,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-non-1-enyl]-5-oxo-cyclopentyl}-hept-2-enoic acid → limaprost (88852-12-4,114868-74-5,75554-85-7,114868-76-7)

Guidance literature:

With hydrogen fluoride; In acetonitrile;

DOI:10.1246/cl.1992.2095

Reference yield:

C32H52O7 → limaprost (88852-12-4,114868-74-5,75554-85-7,114868-76-7)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; at 80 ℃; for 0.5h;

Reference yield:

(E)-7-{(1R,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(3S,5S)-3-(tert-butyl-dimethyl-silanyloxy)-5-methyl-non-1-enyl]-5-oxo-cyclopentyl}-hept-2-enoic acid allyl ester (144877-58-7) → limaprost (88852-12-4,114868-74-5,75554-85-7,114868-76-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / HCO₂H, Et₃N, Pd₂(dibenzylidene)3*CHCl₃ / 2 h / 40 °C

2: 73 percent / aq. HF / acetonitrile

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; formic acid; hydrogen fluoride; triethylamine; In acetonitrile;

DOI:10.1246/cl.1992.2095

upstream raw materials:

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

C₂₉H₅₆O₄Si₂

(3aR,4S,5R,6aS)-4-({[dimethyl(2-methyl-2-propanyl)silyl]oxy}methyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-ol

Downstream raw materials:

(2E)-7-{(1R,2S)-2-[(1E,3S,5S)-3-hydroxy-5-methyl-1-nonenyl]-5-oxo-3-cyclopenten-1-yl}-2-heptenoic acid

C₂₂H₃₆O₅

Refernces

• 1、 -. "Before preparing a Lima intermediate row element, method for preparing the same and before the Lima row element through its method of preparation". . . Retrieved 2017/03/23.
• 2、 -. "Prostaglandin analogues". . . Retrieved 2008/06/13.