(3aR,4R,5R,6aS)-4-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

Base Information

• Chemical Name: (3aR,4R,5R,6aS)-4-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol
• CAS No.: 286840-19-5
• Molecular Formula: C₂₇H₃₈O₇
• Molecular Weight: 474.595

Synonyms:(3aR,4R,5R,6aS)-4-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

Chemical Property of (3aR,4R,5R,6aS)-4-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (3aR,4R,5R,6aS)-4-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol

There total 5 articles about (3aR,4R,5R,6aS)-4-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol 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: 79.0%

(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 (54347-99-8,63324-35-6,64550-46-5,87302-48-5,150577-45-0) → (3aR,4R,5R,6aS)-4-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol (286840-19-5)

Guidance literature:

With diisobutylaluminium hydride; In hexane; toluene; for 0.333333h;

DOI:10.1021/jm00143a018

Reference yield:

methyl 2-phenoxyacetate (2065-23-8) → (3aR,4R,5R,6aS)-4-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol (286840-19-5)

Guidance literature:

Multi-step reaction with 6 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

With 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) → (3aR,4R,5R,6aS)-4-[(E)-(R)-4-Phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-5-(tetrahydro-pyran-2-yloxy)-hexahydro-cyclopenta[b]furan-2-ol (286840-19-5)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/jm00143a018

upstream raw materials:

(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

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

Downstream raw materials:

1-<5α-hydroxy-2β-<(E)-4-phenoxy-3α-tetrahydropyran-2-yloxy-1-butenyl>-3α-tetrahydropyran-2-yloxycyclopent-1α-yl>but-3-yn-2-ol

N-{(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-enoyl}-methanesulfonamide

(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

N-(benzenesulfonyl)-16-phenoxy-ω-tetranor-PGE₂-carboxamide

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