(+/-)-prostaglandin E₂ methyl ester

Base Information

• Chemical Name: (+/-)-prostaglandin E₂ methyl ester
• CAS No.: 23453-26-1
• Molecular Formula: C₂₁H₃₄O₅
• Molecular Weight: 366.498
• Mol file: 23453-26-1.mol

Synonyms:

Chemical Property of (+/-)-prostaglandin E₂ methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (+/-)-prostaglandin E₂ methyl ester

There total 60 articles about (+/-)-prostaglandin E₂ methyl 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: 100.0%

methyl (5Z,13E,15S)-11α,15-bis(dimethyl-t-butylsilyloxy)-9-oxoprosta-5,13-dienoate (66602-10-6,73712-05-7,78856-48-1,78856-50-5,104012-06-8) → (+/-)-prostaglandin E2 methyl ester (23453-26-1,31660-08-9,31687-35-1,31753-17-0,31753-18-1,37495-70-8,37495-91-3,38310-89-3,38873-84-6,39645-55-1,41416-98-2,53275-46-0,53275-48-2,53275-57-3,58691-24-0,62446-69-9,62446-70-2,73712-07-9,104012-07-9,126722-04-1)

Guidance literature:

With hydrogen fluoride; In acetonitrile; at 20 ℃; for 1h;

DOI:10.1039/P19810002049

Reference yield:

7-(tetrahydro-2'H-pyran-2'-yloxy)hept-5-ynoic acid (34506-49-5) → (+/-)-prostaglandin E2 methyl ester (23453-26-1,31660-08-9,31687-35-1,31753-17-0,31753-18-1,37495-70-8,37495-91-3,38310-89-3,38873-84-6,39645-55-1,41416-98-2,53275-46-0,53275-48-2,53275-57-3,58691-24-0,62446-69-9,62446-70-2,73712-07-9,104012-07-9,126722-04-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / p-toluenesulfonic acid hydrate / 36 h / Heating

2: hydrogen / Lindlar catalyst / hexane; ethyl acetate / 0 °C

3: 96 percent / carbon tetrabromide, triphenylphosphine / CH₂Cl₂ / 0.67 h

4: 99.9 percent / NaI / acetone / 0.08 h / with longer reaction time the cis-isomer began to isomerized to trans-isomer

5: 1.) LDA / 1.) THF, -78 deg C, 30 min; 2.)THF, HMPA, -78 deg C, 10 min; -30 deg C, 3 h

6: 95.5 percent / pyridine, 50percent aq. HF / 1.) 0 deg C, 30 min; 2.) rt

7: aluminum amalgam / addition in equal portion after 6 h and 13h; rt 12 h

With pyridine; carbon tetrabromide; aluminium amalgam; hydrogen fluoride; hydrogen; toluene-4-sulfonic acid; triphenylphosphine; sodium iodide; lithium diisopropyl amide; Lindlar's catalyst; In hexane; dichloromethane; ethyl acetate; acetone;

DOI:10.1021/ja00222a034

Reference yield:

methyl 7-hydroxy-5-heptynoate (50781-91-4) → (+/-)-prostaglandin E2 methyl ester (23453-26-1,31660-08-9,31687-35-1,31753-17-0,31753-18-1,37495-70-8,37495-91-3,38310-89-3,38873-84-6,39645-55-1,41416-98-2,53275-46-0,53275-48-2,53275-57-3,58691-24-0,62446-69-9,62446-70-2,73712-07-9,104012-07-9,126722-04-1)

Guidance literature:

Multi-step reaction with 6 steps

1: hydrogen / Lindlar catalyst / hexane; ethyl acetate / 0 °C

2: 96 percent / carbon tetrabromide, triphenylphosphine / CH₂Cl₂ / 0.67 h

3: 99.9 percent / NaI / acetone / 0.08 h / with longer reaction time the cis-isomer began to isomerized to trans-isomer

4: 1.) LDA / 1.) THF, -78 deg C, 30 min; 2.)THF, HMPA, -78 deg C, 10 min; -30 deg C, 3 h

5: 95.5 percent / pyridine, 50percent aq. HF / 1.) 0 deg C, 30 min; 2.) rt

6: aluminum amalgam / addition in equal portion after 6 h and 13h; rt 12 h

With pyridine; carbon tetrabromide; aluminium amalgam; hydrogen fluoride; hydrogen; triphenylphosphine; sodium iodide; lithium diisopropyl amide; Lindlar's catalyst; In hexane; dichloromethane; ethyl acetate; acetone;

DOI:10.1021/ja00222a034

upstream raw materials:

PGH₂ methyl ester

diazomethane

(+/-)-prostaglandin E₂

methyl (5Z,13E)-11α,15-bis(dimethyl-t-butylsilyloxy)-9-oxoprosta-5,13-dienoate

Downstream raw materials:

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