(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

Base Information

• Chemical Name: (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
• CAS No.: 117169-75-2
• Molecular Formula: C₃₇H₆₀O₈
• Molecular Weight: 632.879

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 7 articles about (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 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%

3,4-dihydro-2H-pyran (110-87-2) + 9-acetyl-15-cis-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F2α methyl ester (117169-74-1,117248-78-9) → (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 (117169-75-2,135559-35-2)

Guidance literature:

With triethylamine; toluene-4-sulfonic acid; In dichloromethane; for 0.166667h; Ambient temperature;

DOI:10.1248/cpb.36.1128

Reference yield:

methyl (Z)-7-[(1R,2R,3R,5S)-5-acetoxy-2-formyl-3-(2-tetrahydropyranyloxy)cyclopentyl]-5-heptenate (61218-06-2) → (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 (117169-75-2,135559-35-2)

Guidance literature:

Multi-step reaction with 4 steps

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

2: 92 percent / 65percent aq. acetic acid / tetrahydrofuran / 1.5 h / 40 °C

3: diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide / toluene / 1.) -78 deg C, 15 min; 2.) -20 deg C, 2 h

4: Et₃N / p-toluenesulfonic acid / CH₂Cl₂ / 0.17 h / Ambient temperature

With sodium hydride; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; acetic acid; triethylamine; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1248/cpb.36.1128

Reference yield:

methyl cis-4-n-propylcyclohexanecarboxylate (101691-32-1) → (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 (117169-75-2,135559-35-2)

Guidance literature:

Multi-step reaction with 5 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

3: 92 percent / 65percent aq. acetic acid / tetrahydrofuran / 1.5 h / 40 °C

4: diisobutylaluminum 2,6-di-tert-butyl-4-methylphenoxide / toluene / 1.) -78 deg C, 15 min; 2.) -20 deg C, 2 h

5: Et₃N / p-toluenesulfonic acid / CH₂Cl₂ / 0.17 h / Ambient temperature

With n-butyllithium; sodium hydride; diisobutyl(2,6-di-tert-butyl-4- methylphenoxy)aluminum; acetic acid; triethylamine; toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1248/cpb.36.1128

upstream raw materials:

3,4-dihydro-2H-pyran

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

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

methyl cis-4-n-propylcyclohexanecarboxylate

Downstream raw materials:

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

(Z)-7-{(1R,2R,3R,5S)-5-Azido-3-hydroxy-2-[(E)-(S)-3-hydroxy-3-(4-propyl-cyclohexyl)-propenyl]-cyclopentyl}-hept-5-enoic acid methyl ester

15-cis-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanor-9-deoxy-6,9α-nitriloprostaglandin F₁ methyl ester

9-deoxy-9β-tosyloxy-15-cis-(4-n-propylcyclohexyl)-16,17,18,19,20-pentanorprostaglandin F₂ methyl ester 11,15-bistetrahydropyranyl ether

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