Alprostadil ethyl ester

Base Information

• Chemical Name: Alprostadil ethyl ester
• CAS No.: 35900-16-4
• Molecular Formula: C₂₂H₃₈O₅
• Molecular Weight: 382.541
• European Community (EC) Number: 806-708-3
• UNII: IG6WR57RZT
• DSSTox Substance ID: DTXSID10189476
• Nikkaji Number: J562.382K
• Wikidata: Q27280712
• Mol file: 35900-16-4.mol

Synonyms:PGE1 ethyl ester;prostaglandin E1 ethyl ester

Chemical Property of Alprostadil ethyl ester

Chemical Property:

• PSA: 83.83000
• LogP: 3.95360
• Storage Temp.: −20°C
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 15
• Exact Mass: 382.27192431
• Heavy Atom Count: 27
• Complexity: 460

Purity/Quality:

>95% ^*data from raw suppliers

Prostaglandin E1 ethyl ester ≥95% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: F,Xn,Xi
• Statements: 11-20/21/22-36/37/38-67-66-36
• Safety Statements: 16-26-36/37/39-33-29

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCC(C=CC1C(CC(=O)C1CCCCCCC(=O)OCC)O)O
• Isomeric SMILES: CCCCC[C@@H](/C=C/[C@H]1[C@@H](CC(=O)[C@@H]1CCCCCCC(=O)OCC)O)O

Technology Process of Alprostadil ethyl ester

There total 10 articles about Alprostadil ethyl ester 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: 29.8%

ethyl bromide (74-96-4) + ALPROSTADIL (745-65-3) → ethyl 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoate (35900-16-4)

Guidance literature:

With tetrabutylammomium bromide; potassium hydroxide; In tetrahydrofuran; diethyl ether; at 20 ℃; for 1h; Cooling with ice;

Reference yield:

1-octyn-3-ol (32556-71-1,37911-28-7) → 7-[(2S,3S)-3-Hydroxy-2-((E)-(S)-3-hydroxy-oct-1-enyl)-5-oxo-cyclopentyl]-heptanoic acid ethyl ester (22469-24-5,35900-16-4,55253-43-5)

Guidance literature:

Multi-step reaction with 3 steps

1: (i) (iBu)3Al, DIBAH, heptane, (ii) I₂, THF

2: aq. HCl

3: (i) Li, Et₂O, (ii) (nBu)3P*CuI, (iii) /BRN= 1435951/

With hydrogenchloride;

DOI:10.1021/ja00837a028

Reference yield:

1-octyn-3-ol (32556-71-1,37911-28-7) → ethyl 7-[(1R,2R,3R)-3-hydroxy-2-[(3S)-3-hydroxyoct-1-en-1-yl]-5-oxocyclopentyl]heptanoate (35900-16-4)

Guidance literature:

Multi-step reaction with 3 steps

1: (i) (iBu)3Al, DIBAH, heptane, (ii) I₂, THF

2: aq. HCl

3: (i) Li, Et₂O, (ii) (nBu)3P*CuI, (iii) /BRN= 1435951/

With hydrogenchloride;

DOI:10.1021/ja00837a028

upstream raw materials:

2-(6-ethoxycarbonylhexyl)-4-(tetrahydropyran-2-yloxy)cyclopent-2-enone

(S)-3-(1-ethoxy-ethoxy)-1t-iodo-oct-1-ene

1-octyn-3-ol

(S)-(E)-(+)-1-Iodo-1-octen-3-ol

Refernces

• 1、 -. "A prostaglandin E1 methyl ester freeze dried preparation for injection and its preparation and use (by machine translation)". Paragraph 0058-0063. . Retrieved 2019/03/23.
• 2、 Sih,Salomon,Price,Sood,Peruzzotti. "Stereospecific total synthesis of prostaglandins via reaction of alpha-alkylcyclopentenones with organocuprates.". . p. 857 - 865. Retrieved 2007/10/11.