(1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one

Base Information

• Chemical Name: (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one
• CAS No.: 145773-21-3
• Molecular Formula: C₁₈H₂₄O₄
• Molecular Weight: 304.386
• Mol file: 145773-21-3.mol

Synonyms:(1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one

Chemical Property of (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one

There total 9 articles about (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-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: 85.0%

(1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one (145773-20-2) → (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one (145773-21-3)

Guidance literature:

With potassium carbonate; In methanol; for 6h; Ambient temperature;

DOI:10.1021/jm00054a008

Reference yield:

(3aR,4R,5R,6aS)-4-[3S-(p-nitrobenzoyloxy)-5-phenyl-1E-pentenyl]-5-(benzoyloxy)-hexahydro-2H-cyclopenta[b]furan-2-one (1355995-17-3) → (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one (145773-21-3)

Guidance literature:

(3aR,4R,5R,6aS)-4-[3S-(p-nitrobenzoyloxy)-5-phenyl-1E-pentenyl]-5-(benzoyloxy)-hexahydro-2H-cyclopenta[b]furan-2-one; With methanol; potassium carbonate; In dichloromethane; at 25 - 30 ℃;

With hydrogenchloride; In dichloromethane; water; pH=4;

Reference yield:

(-)-Corey lactone 5-(4-phenylbenzoate) (31752-99-5) → (1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7(R)-hydroxy-2-oxabicyclo<3.3.0>octan-3-one (145773-21-3)

Guidance literature:

Multi-step reaction with 5 steps

1: DCC, phosphoric acid / 1,2-dimethoxy-ethane / a) 18 deg C, 30 min, b) RT, 2 h

2: 1.) NaH / 1.) DME, RT, 1 h, 2.) DME, a) 0 deg C, 30 min, b) RT, 2 h

3: 52 percent / lithium tri-sec-butylborohydride (lithium selectride) / tetrahydrofuran; diethyl ether / 1 h / -78 - -75 °C

4: 78.4 percent / H₂, 1 M NaOH / 10percent Pd/C / ethanol / 6 h

5: 85 percent / K₂CO₃ / methanol / 6 h / Ambient temperature

With sodium hydroxide; phosphoric acid; hydrogen; L-Selectride; sodium hydride; potassium carbonate; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol;

DOI:10.1021/jm00054a008

upstream raw materials:

(1S,5R,6R,7R)-6-<(3R)-3-hydroxy-5-phenyl-1-pentyl>-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one

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

benzyl bromide

(1S,5R,6R,7R)-6-(3-oxo-5-phenyl-1E-pentenyl)-7-<(4-phenylbenzoyl)oxy>-2-oxabicyclo<3.3.0>octan-3-one

Downstream raw materials:

latanoprost acid

latanoprost

(3aR,4R,5R,6aS)-hexahydro-4-[(1E,3S)-3-hydroxy-5-phenyl-1-penten-1-yl]-2H-cyclopenta[b]furan-2,5-diol