(Z)-7-[(1R,2R,3R,5S)-2-[(E)-5-(4-azidophenyl)-3-hydroxypent-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoic acid

Base Information

• Chemical Name: (Z)-7-[(1R,2R,3R,5S)-2-[(E)-5-(4-azidophenyl)-3-hydroxypent-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoic acid
• CAS No.: 117625-46-4
• Molecular Formula: C₂₃H₃₁N₃O₅
• Molecular Weight: 429.516
• Mol file: 117625-46-4.mol

Synonyms:17-(4-azidophenyl)-18,19,20-trinorprostaglandin E2;Az-18,19,20-TN-PGE2

Chemical Property of (Z)-7-[(1R,2R,3R,5S)-2-[(E)-5-(4-azidophenyl)-3-hydroxypent-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoic acid

Chemical Property:

• PSA: 147.74000
• LogP: 3.48996
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 429.22637110
• Heavy Atom Count: 31
• Complexity: 654

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C1O)C=CC(CCC2=CC=C(C=C2)N=[N+]=[N-])O)CC=CCCCC(=O)O)O
• Isomeric SMILES: C1[C@@H]([C@@H]([C@H]([C@@H]1O)/C=C/C(CCC2=CC=C(C=C2)N=[N+]=[N-])O)C/C=C\CCCC(=O)O)O

Technology Process of (Z)-7-[(1R,2R,3R,5S)-2-[(E)-5-(4-azidophenyl)-3-hydroxypent-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoic acid

There total 14 articles about (Z)-7-[(1R,2R,3R,5S)-2-[(E)-5-(4-azidophenyl)-3-hydroxypent-1-enyl]-3,5-dihydroxycyclopentyl]hept-5-enoic acid 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:

(-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5) → (Z)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-phenyl)-3-hydroxy-pent-1-enyl]-3,5-dihydroxy-cyclopentyl}-hept-5-enoic acid (117625-46-4)

Guidance literature:

Multi-step reaction with 10 steps

1: chromium trioxide-dipyridine complex, Celite / CH₂Cl₂ / 0.33 h / 0 °C

2: 1) NaH / 1) 1,2-dimethoxyethane, toluene, 25 deg C, 30 min, 2) 25 deg C, 2 h

3: 47 percent / NaBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 0.17 h / 25 °C

4: K₂CO₃, MeOH

5: PPTS

6: DiBAL

10: LiOH

With methanol; lithium hydroxide; sodium tetrahydroborate; cerium(III) chloride; 2,2'-bipyridine-chromium(VI) oxide; Celite; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm00121a046

Reference yield:

methyl 3-(4-aminophenyl)propionate (35418-07-6) → (Z)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-phenyl)-3-hydroxy-pent-1-enyl]-3,5-dihydroxy-cyclopentyl}-hept-5-enoic acid (117625-46-4)

Guidance literature:

Multi-step reaction with 11 steps

1: pyridine / 20 h / 25 °C

2: 1) n-BuLi / 1) THF, hexane, -78 deg C, 30 min, 2) toluene, THF, -78 deg C, 30 min

3: 1) NaH / 1) 1,2-dimethoxyethane, toluene, 25 deg C, 30 min, 2) 25 deg C, 2 h

4: 47 percent / NaBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 0.17 h / 25 °C

5: K₂CO₃, MeOH

6: PPTS

7: DiBAL

11: LiOH

With pyridine; methanol; lithium hydroxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol;

DOI:10.1021/jm00121a046

Reference yield:

3-(4-aminophenyl)propionic acid (2393-17-1) → (Z)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-phenyl)-3-hydroxy-pent-1-enyl]-3,5-dihydroxy-cyclopentyl}-hept-5-enoic acid (117625-46-4)

Guidance literature:

Multi-step reaction with 12 steps

1: HCl(g) / 20 h / Heating

2: pyridine / 20 h / 25 °C

3: 1) n-BuLi / 1) THF, hexane, -78 deg C, 30 min, 2) toluene, THF, -78 deg C, 30 min

4: 1) NaH / 1) 1,2-dimethoxyethane, toluene, 25 deg C, 30 min, 2) 25 deg C, 2 h

5: 47 percent / NaBH₄, CeCl₃*7H₂O / methanol; tetrahydrofuran / 0.17 h / 25 °C

6: K₂CO₃, MeOH

7: PPTS

8: DiBAL

12: LiOH

With pyridine; hydrogenchloride; methanol; lithium hydroxide; sodium tetrahydroborate; n-butyllithium; cerium(III) chloride; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; In tetrahydrofuran; methanol;

DOI:10.1021/jm00121a046

upstream raw materials:

(Z)-7-{(1R,2R,3R,5S)-2-[(E)-(S)-5-(4-Azido-phenyl)-3-hydroxy-pent-1-enyl]-3,5-dihydroxy-cyclopentyl}-hept-5-enoic acid methyl ester

(-)-Corey lactone 5-(4-phenylbenzoate)

methyl 3-(4-aminophenyl)propionate

3-(4-aminophenyl)propionic acid

Refernces