9-acetyl-15-cis-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanor-15-dehydroprostaglandin F_2α methyl ester 11-tetrahydropyranyl ether

Base Information

• Chemical Name: 9-acetyl-15-cis-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanor-15-dehydroprostaglandin F_2α methyl ester 11-tetrahydropyranyl ether
• CAS No.: 101691-34-3
• Molecular Formula: C₃₂H₅₀O₇
• Molecular Weight: 546.745
• Mol file: 101691-34-3.mol

Synonyms:9-acetyl-15-cis-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanor-15-dehydroprostaglandin F_2α methyl ester 11-tetrahydropyranyl ether

Chemical Property of 9-acetyl-15-cis-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanor-15-dehydroprostaglandin F_2α methyl ester 11-tetrahydropyranyl ether

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-acetyl-15-cis-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanor-15-dehydroprostaglandin F_2α methyl ester 11-tetrahydropyranyl ether

There total 3 articles about 9-acetyl-15-cis-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanor-15-dehydroprostaglandin F_2α methyl ester 11-tetrahydropyranyl ether 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: 81.0%

methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate (61218-06-2) + dimethyl 2-oxo-2-cis-(4-n-propylcyclohexyl)ethyl phosphonate (101691-28-5) → 9-acetyl-15-cis-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanor-15-dehydroprostaglandin F2α methyl ester 11-tetrahydropyranyl ether (101691-34-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1248/cpb.36.1128

Reference yield:

methyl cis-4-n-propylcyclohexanecarboxylate (101691-32-1) → 9-acetyl-15-cis-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanor-15-dehydroprostaglandin F2α methyl ester 11-tetrahydropyranyl ether (101691-34-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min; 2.) THF, hexane, -78 deg C, 2.5 h

2: 81 percent / sodium hydride / tetrahydrofuran / 1 h / Ambient temperature

With n-butyllithium; sodium hydride; In tetrahydrofuran;

DOI:10.1248/cpb.36.1128

Reference yield:

methyl trans-4-n-propylcyclohexanecarboxylate (117169-72-9) → 9-acetyl-15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanor-15-dehydroprostaglandin F2α methyl ester 11-tetrahydropyranyl ether (101691-34-3,135559-33-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 15 min; 2.) THF, hexane, -78 deg C, 2.5 h

2: sodium hydride / tetrahydrofuran / 1 h / Ambient temperature

With n-butyllithium; sodium hydride; In tetrahydrofuran;

DOI:10.1248/cpb.36.1128

upstream raw materials:

methyl trans-4-n-propylcyclohexanecarboxylate

methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate

dimethyl 2-oxo-2-cis-(4-n-propylcyclohexyl)ethyl phosphonate

methyl cis-4-n-propylcyclohexanecarboxylate

Downstream raw materials:

(Z)-7-[(1R,2R,3R,5S)-5-Acetoxy-2-[(E)-(S)-3-(4-propyl-cyclohexyl)-3-(tetrahydro-pyran-2-yloxy)-propenyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid methyl ester

9-deoxy-9β-tosyloxy-15-trans-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F₂ methyl ester

15-trans-(4-α-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F_2α methyl ester

9-acetyl-15α-cis-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F_2α methyl ester