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

Base Information

• Chemical Name: 10-nor-9,11-secoprostaglandin F_2α 15-acetate 9,11-ditosylate methyl ester
• CAS No.: 80559-71-3
• Molecular Formula: C₃₆H₅₀O₁₀S₂
• Molecular Weight: 706.919
• Mol file: 80559-71-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 12 articles about 10-nor-9,11-secoprostaglandin F_2α 15-acetate 9,11-ditosylate 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: 11.4%

10-nor-9,11-secoprostaglandin F2 15-acetate methyl ester (80559-69-9) → 10-oxa-9,11-dideoxyprostaglandin F2α 15-acetate methyl ester (80559-72-4) + 10-nor-9,11-secoprostaglandin F2α 15-acetate 9,11-ditosylate methyl ester (80559-71-3)

Guidance literature:

With pyridine; p-toluenesulfonyl chloride; for 24h; Ambient temperature;

DOI:10.1021/ja00370a029

Reference yield: 3.0%

10-nor-9,11-secoprostaglandin F2 15-acetate methyl ester (80559-69-9) + p-toluenesulfonyl chloride (98-59-9) → 10-oxa-9,11-dideoxyprostaglandin F2α 15-acetate methyl ester (80559-72-4) + 10-nor-9,11-secoprostaglandin F2α 15-acetate 9,11-ditosylate methyl ester (80559-71-3)

Guidance literature:

With pyridine; for 24h;

DOI:10.1021/ja00370a029

Reference yield:

(Z)-7-[(1S,2R,3R,5S)-2-((E)-(S)-3-Hydroxy-oct-1-enyl)-4-oxo-6-oxa-bicyclo[3.1.0]hex-3-yl]-hept-5-enoic acid methyl ester (38310-84-8) → 10-nor-9,11-secoprostaglandin F2α 15-acetate 9,11-ditosylate methyl ester (80559-71-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 59 percent / sodium borohydride / methanol / 2 h / Ambient temperature

2: 1.) periodic acid, 2.) sodium borohydride / 1.) THF, water, 60 deg C, 5 h, 2.) isopropyl alcohol, room temperature, 2 h

3: p-toluenesulfonic acid / 3 h / 0 - 5 °C

4: 82 percent / pyridine / 2 h / Ambient temperature

5: 98 percent / acetic acid / H₂O / 4 h / Ambient temperature

6: 11.4 percent / pyridine, p-toluenesulfonyl chloride / 24 h / Ambient temperature

With pyridine; sodium tetrahydroborate; toluene-4-sulfonic acid; acetic acid; periodic acid; p-toluenesulfonyl chloride; In methanol; water;

DOI:10.1021/ja00370a029

upstream raw materials:

10-nor-9,11-secoprostaglandin F₂ 15-acetate methyl ester

p-toluenesulfonyl chloride

(Z)-7-[(1S,2R,3R,5S)-2-((E)-(S)-3-Hydroxy-oct-1-enyl)-4-oxo-6-oxa-bicyclo[3.1.0]hex-3-yl]-hept-5-enoic acid methyl ester

10α,11α-epoxy-11-deoxyprostaglandin F_2α methyl ester

Downstream raw materials:

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