(5Z,13E)-15-acetyl-oxy-9-oxo-prosta-5,10,13-trien-1-oic acid methyl ester

Base Information

• Chemical Name: (5Z,13E)-15-acetyl-oxy-9-oxo-prosta-5,10,13-trien-1-oic acid methyl ester
• CAS No.: 36323-03-2
• Molecular Formula: C₂₃H₃₄O₅
• Molecular Weight: 390.52
• Mol file: 36323-03-2.mol

Synonyms:(5Z,13E)-15-acetyl-oxy-9-oxo-prosta-5,10,13-trien-1-oic acid methyl ester

Chemical Property of (5Z,13E)-15-acetyl-oxy-9-oxo-prosta-5,10,13-trien-1-oic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5Z,13E)-15-acetyl-oxy-9-oxo-prosta-5,10,13-trien-1-oic acid methyl ester

There total 1 articles about (5Z,13E)-15-acetyl-oxy-9-oxo-prosta-5,10,13-trien-1-oic acid 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:

diazomethane (186581-53-3,908094-01-9,334-88-3) + 13,14-cis-PGA2 (55392-90-0,58685-03-3,63141-11-7,64338-92-7) → (Z)-7-[(1R,2S)-2-((Z)-(R)-3-Acetoxy-oct-1-enyl)-5-oxo-cyclopent-3-enyl]-hept-5-enoic acid methyl ester (25488-91-9,36323-03-2,58685-04-4,59659-05-1,64338-95-0)

Guidance literature:

In diethyl ether;

DOI:10.1021/ja00460a037

Reference yield:

(5Z,13E)-15-acetyl-oxy-9-oxo-prosta-5,10,13-trien-1-oic acid methyl ester (36323-03-2) → 10-nor-9,11-secoprostaglandin F2 9,11-ditosylate methyl ester (80559-76-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) aq. hydrogen peroxide, aq. lithium hydroxide, 2.) sodium borohydride / 1.) isopropyl alcohol, -30 - -40 deg C, 90 min, 2.) 40 min

2: 22 percent / periodic acid / tetrahydrofuran; H₂O / 5 h / 70 °C

3: 11.4 percent / pyridine, p-toluenesulfonyl chloride / 24 h / Ambient temperature

4: 95 percent / sodium methoxide / methanol / 2 h / 25 °C

With pyridine; lithium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; sodium methylate; periodic acid; p-toluenesulfonyl chloride; In tetrahydrofuran; methanol; water;

DOI:10.1021/ja00370a029

Reference yield:

(5Z,13E)-15-acetyl-oxy-9-oxo-prosta-5,10,13-trien-1-oic acid methyl ester (36323-03-2) → 10-nor-9,11-secoprostaglandin F2α 15-acetate 9,11-ditosylate methyl ester (80559-71-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) aq. hydrogen peroxide, aq. lithium hydroxide, 2.) sodium borohydride / 1.) isopropyl alcohol, -30 - -40 deg C, 90 min, 2.) 40 min

2: 22 percent / periodic acid / tetrahydrofuran; H₂O / 5 h / 70 °C

3: 11.4 percent / pyridine, p-toluenesulfonyl chloride / 24 h / Ambient temperature

With pyridine; lithium hydroxide; sodium tetrahydroborate; dihydrogen peroxide; periodic acid; p-toluenesulfonyl chloride; In tetrahydrofuran; water;

DOI:10.1021/ja00370a029

upstream raw materials:

diazomethane

13,14-cis-PGA₂

Downstream raw materials:

10-nor-9,11-secoprostaglandin F₂ 9,11-ditosylate methyl ester

10-nor-9,11-secoprostaglandin F_2α 15-acetate 9,11-ditosylate methyl ester

(+)-11a-homoprostaglandin A₂ acetate methyl ester

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