(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

Base Information

• Chemical Name: (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
• CAS No.: 54347-99-8
• Molecular Formula: C₂₇H₃₆O₇
• Molecular Weight: 472.579
• Mol file: 54347-99-8.mol

Synonyms:

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (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

There total 4 articles about (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 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: 95.0%

3,4-dihydro-2H-pyran (110-87-2) + (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) → (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)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 0.5h;

DOI:10.1021/jm00143a018

Reference yield:

methyl 2-phenoxyacetate (2065-23-8) → (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)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/jm00143a018

Reference yield:

dimethyl (3-phenoxy-2-oxopropyl)phosphonate (40665-68-7) → (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)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1021/jm00143a018

upstream raw materials:

3,4-dihydro-2H-pyran

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

methyl 2-phenoxyacetate

dimethyl (3-phenoxy-2-oxopropyl)phosphonate

Downstream raw materials:

(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

(3S)-3-Bromo-4-<(1R,2R,3R,5S)-5-<(tert-butyldimethylsilyl)oxy>-2-<(E)-(3R)-4-phenoxy-3-<(tetrahydro-2H-pyran-2-yl)oxy>-1-butenyl>-3-<(tetrahydro-2H-pyran-2-yl)oxy>cyclopentyl>but-1-yne

2-[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-ethanol

[(1R,2R,3R,5S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-[(E)-(R)-4-phenoxy-3-(tetrahydro-pyran-2-yloxy)-but-1-enyl]-3-(tetrahydro-pyran-2-yloxy)-cyclopentyl]-acetaldehyde