N-{(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-enoyl}-methanesulfonamide

Base Information

• Chemical Name: N-{(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-enoyl}-methanesulfonamide
• CAS No.: 64282-81-1
• Molecular Formula: C₃₃H₄₉NO₉S
• Molecular Weight: 635.819

Synonyms:N-{(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-enoyl}-methanesulfonamide

Chemical Property of N-{(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-enoyl}-methanesulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-{(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-enoyl}-methanesulfonamide

There total 5 articles about N-{(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-enoyl}-methanesulfonamide 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) → N-{(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-enoyl}-methanesulfonamide (64282-81-1)

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, 2 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) → N-{(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-enoyl}-methanesulfonamide (64282-81-1)

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, 2 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)-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) → N-{(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-enoyl}-methanesulfonamide (64282-81-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / diisobutylaluminum hydride / toluene; hexane / 0.33 h

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

With sodium methylsulfinylcarbanide; diisobutylaluminium hydride; In hexane; toluene;

DOI:10.1021/jm00143a018

upstream raw materials:

[4-(methanesulfonylaminocarbonyl)-n-butyl]triphenylphosphonium bromide

(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

methyl 2-phenoxyacetate

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Downstream raw materials:

N-(methanesulfonyl)-16-phenox-ω-tetranor-PGF_2α-carboxamide

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

N-(methanesulfonyl)-16-phenoxy-ω-tetranor-PGB₂-carboxamide

N-(methanesulfonyl)-16-phenoxy-ω-tetranor-PGA₂-carboxamide

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