(Z)-7-[(1R,2R,3R,5S)-5-Hydroxy-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid

Base Information

• Chemical Name: (Z)-7-[(1R,2R,3R,5S)-5-Hydroxy-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid
• CAS No.: 62989-31-5
• Molecular Formula: C₃₂H₄₆O₈
• Molecular Weight: 558.712

Synonyms:(Z)-7-[(1R,2R,3R,5S)-5-Hydroxy-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid

Chemical Property of (Z)-7-[(1R,2R,3R,5S)-5-Hydroxy-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (Z)-7-[(1R,2R,3R,5S)-5-Hydroxy-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid

There total 5 articles about (Z)-7-[(1R,2R,3R,5S)-5-Hydroxy-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-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:

methyl 2-phenoxyacetate (2065-23-8) → (Z)-7-[(1R,2R,3R,5S)-5-Hydroxy-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid (62989-31-5)

Guidance literature:

Multi-step reaction with 7 steps

1: tetrahydrofuran / -78 °C

2: 1.) NaH / 1.) THF, 90 min, 2.) THF, 30 min

3: 25 percent / lithium triethylborohydride / tetrahydrofuran / 0.5 h

4: potassium carbonate / methanol; tetrahydrofuran / 2.5 h

5: 95 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.5 h

6: 79 percent / diisobutylaluminum hydride / toluene; hexane / 0.33 h

7: 1.) sodium methylsulfinylcarbanide / 1.) Me₂SO, 2.) Me₂SO, 6 h

With sodium methylsulfinylcarbanide; sodium hydride; diisobutylaluminium hydride; lithium triethylborohydride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;

DOI:10.1021/jm00143a018

Reference yield:

dimethyl (3-phenoxy-2-oxopropyl)phosphonate (40665-68-7) → (Z)-7-[(1R,2R,3R,5S)-5-Hydroxy-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid (62989-31-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH / 1.) THF, 90 min, 2.) THF, 30 min

2: 25 percent / lithium triethylborohydride / tetrahydrofuran / 0.5 h

3: potassium carbonate / methanol; tetrahydrofuran / 2.5 h

4: 95 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.5 h

5: 79 percent / diisobutylaluminum hydride / toluene; hexane / 0.33 h

6: 1.) sodium methylsulfinylcarbanide / 1.) Me₂SO, 2.) Me₂SO, 6 h

With sodium methylsulfinylcarbanide; sodium hydride; diisobutylaluminium hydride; lithium triethylborohydride; potassium carbonate; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene;

DOI:10.1021/jm00143a018

Reference yield:

(3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-hexahydro-cyclopenta[b]furan-2-one (51638-93-8) → (Z)-7-[(1R,2R,3R,5S)-5-Hydroxy-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid (62989-31-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 95 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.5 h

2: 79 percent / diisobutylaluminum hydride / toluene; hexane / 0.33 h

3: 1.) sodium methylsulfinylcarbanide / 1.) Me₂SO, 2.) Me₂SO, 6 h

With sodium methylsulfinylcarbanide; diisobutylaluminium hydride; toluene-4-sulfonic acid; In hexane; dichloromethane; toluene;

DOI:10.1021/jm00143a018

upstream raw materials:

methyl 2-phenoxyacetate

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

(3aR,4R,5R,6aS)-5-Hydroxy-4-((E)-(R)-3-hydroxy-4-phenoxy-but-1-enyl)-hexahydro-cyclopenta[b]furan-2-one

(3aR,4R,5R,6aS)-Hexahydro-4-<(E)-(3R)-4-phenoxy-3-<(tetrahydro-2H-pyran-2-yl)oxy>-1-butenyl>-5-<(tetrahydro-2H-pyran-2-yl)oxy>-2H-cyclopentafuran-2-one

Downstream raw materials:

(Z)-7-[(1R,2R,3R)-5-Oxo-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-hept-5-enoic acid

16-phenoxy-ω-tetranor-PGE₂

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