(4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (E,3S)-3-hydroxy-5-oxo-7-phenyl-6-heptenoate

Base Information

• Chemical Name: (4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (E,3S)-3-hydroxy-5-oxo-7-phenyl-6-heptenoate
• CAS No.: 135942-74-4
• Molecular Formula: C₃₃H₃₆O₄
• Molecular Weight: 496.646
• Mol file: 135942-74-4.mol

Synonyms:(4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (E,3S)-3-hydroxy-5-oxo-7-phenyl-6-heptenoate

Chemical Property of (4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (E,3S)-3-hydroxy-5-oxo-7-phenyl-6-heptenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (E,3S)-3-hydroxy-5-oxo-7-phenyl-6-heptenoate

There total 2 articles about (4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (E,3S)-3-hydroxy-5-oxo-7-phenyl-6-heptenoate 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%

(4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (E)-7-phenyl-3,5-dioxo-6-heptenoate (135942-64-2) → (4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (E,3S)-3-hydroxy-5-oxo-7-phenyl-6-heptenoate (135942-74-4)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃;

DOI:10.1021/jo00020a008

Reference yield: 85.0%

(4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (E)-7-phenyl-3,5-dioxo-6-heptenoate (135942-64-2) → (4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (E,3S)-3-hydroxy-5-oxo-7-phenyl-6-heptenoate (135942-74-4) + (4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (E,3R)-3-hydroxy-5-oxo-7-phenyl-6-heptenoate (136030-17-6)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -78 ℃; for 4h;

DOI:10.1246/bcsj.68.350

Reference yield:

(4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (E,3S)-3-hydroxy-5-oxo-7-phenyl-6-heptenoate (135942-74-4) → 4(S),6(S)-4-hydroxy-6-(2-phenylethyl)tetrahydropyran-2-one (119239-93-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) Et₂BOMe 2) NaBH₄ / 1) THF, MeOH, r.t. 2) a) -78 deg C b) r.t., overnight

2: hydrogenation

3: 1M aq. NaOH / methanol / Ambient temperature

4: toluene / 110 °C

With sodium hydroxide; sodium tetrahydroborate; diethyl methoxy borane; In methanol; toluene;

DOI:10.1021/jo00020a008

upstream raw materials:

(4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (E)-7-phenyl-3,5-dioxo-6-heptenoate

Downstream raw materials:

(4R)-4,7,7-trimethyl-3-exo-(1-naphthyl)bicyclo<2.2.1>heptan-2-exo-yl (3S,5R,6E)-7-phenyl-3,5-dihydroxy-6-heptenoate

methyl (3S,5R,6E)-7-phenyl-3,5-dihydroxy-6-heptenoate

4(S),6(S)-4-hydroxy-6-(2-phenylethyl)tetrahydropyran-2-one

(4S,6R,E)-4-hydroxy-6-(2-phenylethenyl)-tetrahydropyran-2-one