(1R,2R,3R,5R,8R)-(+)-8-Benzoyloxy-2,7,7-trimethylbicyclo<3.3.0>octan-3-ol

Base Information

• Chemical Name: (1R,2R,3R,5R,8R)-(+)-8-Benzoyloxy-2,7,7-trimethylbicyclo<3.3.0>octan-3-ol
• CAS No.: 119433-11-3
• Molecular Formula: C₁₈H₂₄O₃
• Molecular Weight: 288.387
• Mol file: 119433-11-3.mol

Synonyms:(1R,2R,3R,5R,8R)-(+)-8-Benzoyloxy-2,7,7-trimethylbicyclo<3.3.0>octan-3-ol

Chemical Property of (1R,2R,3R,5R,8R)-(+)-8-Benzoyloxy-2,7,7-trimethylbicyclo<3.3.0>octan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3R,5R,8R)-(+)-8-Benzoyloxy-2,7,7-trimethylbicyclo<3.3.0>octan-3-ol

There total 28 articles about (1R,2R,3R,5R,8R)-(+)-8-Benzoyloxy-2,7,7-trimethylbicyclo<3.3.0>octan-3-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: 91.0%

Benzoic acid (1R,3aR,5R,6R,6aR)-2,2,6-trimethyl-5-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl ester (119337-77-8,135093-34-4,135093-35-5) → (1R,2R,3R,5R,8R)-(+)-8-Benzoyloxy-2,7,7-trimethylbicyclo<3.3.0>octan-3-ol (119433-11-3)

Guidance literature:

With acetic acid; In tetrahydrofuran; water; for 16h; Ambient temperature;

Reference yield:

(2aSR,4RS,4aSR,6aSR,6bRS)-octahydro-6,6-dimethyl-2-oxo-2H-pentaleno<1,6-bc>furan-4-carboxylic acid (82873-74-3) → (1RS,2RS,3aRS,6RS,6aRS)-6-benzoyloxy-octahydro-2-hydroxy-1,5,5-trimethylpentalene (90546-13-7,119433-11-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) pyridine, Cu(OAc)2; 2.) Pb(OAc)4 / 1.) benzene, 30 min; 2a.) 2.5 h, dark, b.) benzene, reflux, 30 min

2: 1.) t-AmONa; 2.) water / 1.) DMSO, 18 h, r.t.; 2.) 6 h; 3.) 24 h

3: 92 percent / Jones reagent / acetone / 0.5 h / 0 °C

4: 23.9 percent / 0.82 M AlH₃ / tetrahydrofuran / 3 h / 0 °C

5: 86 percent / LiCl, methanesulfonyl chloride / dimethylformamide; various solvent(s) / 1.5 h / 0 °C

6: 8.0 g / LiAlH₄ / tetrahydrofuran / 5 h / Ambient temperature

7: 95 percent / pyridine / 12 h / 0 °C

8: 82 percent / KO₂ / dibenzo-18-crown-6-ether / 1,2-dimethoxy-ethane; dimethylsulfoxide / 48 h / Ambient temperature

9: 96 percent / pyridine / 6 h / Ambient temperature

10: 1.) BH₃; 2.) 2 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C, 3 h; 2.) water, 10 min

With pyridine; aluminium hydride; lead(IV) acetate; sodium hydroxide; lithium aluminium tetrahydride; jones reagent; copper diacetate; borane; water; dihydrogen peroxide; sodium tert-pentoxide; methanesulfonyl chloride; lithium chloride; dibenzo-18-crown-6; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;

DOI:10.1016/0040-4020(84)85126-1

Reference yield:

cis-3,3a,4,5,6,6a-hexahydro-5,5-dimethyl-6-oxo-1-pentalenecarboxylic acid methyl ester (90546-09-1) → (1RS,2RS,3aRS,6RS,6aRS)-6-benzoyloxy-octahydro-2-hydroxy-1,5,5-trimethylpentalene (90546-13-7,119433-11-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 23.9 percent / 0.82 M AlH₃ / tetrahydrofuran / 3 h / 0 °C

2: 86 percent / LiCl, methanesulfonyl chloride / dimethylformamide; various solvent(s) / 1.5 h / 0 °C

3: 8.0 g / LiAlH₄ / tetrahydrofuran / 5 h / Ambient temperature

4: 95 percent / pyridine / 12 h / 0 °C

5: 82 percent / KO₂ / dibenzo-18-crown-6-ether / 1,2-dimethoxy-ethane; dimethylsulfoxide / 48 h / Ambient temperature

6: 96 percent / pyridine / 6 h / Ambient temperature

7: 1.) BH₃; 2.) 2 N NaOH, 30percent H₂O₂ / 1.) THF, 0 deg C, 3 h; 2.) water, 10 min

With aluminium hydride; sodium hydroxide; lithium aluminium tetrahydride; borane; dihydrogen peroxide; methanesulfonyl chloride; lithium chloride; dibenzo-18-crown-6; In tetrahydrofuran; pyridine; 1,2-dimethoxyethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(84)85126-1

upstream raw materials:

(3aRS,6RS,6aRS)-6-benzoyloxy-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethylpentalene

Benzoic acid (1R,3aR,5R,6R,6aR)-2,2,6-trimethyl-5-(tetrahydro-pyran-2-yloxy)-octahydro-pentalen-1-yl ester

benzoyl chloride

(3aR,5R,6R,6aR)-6-Methyl-5-(tetrahydro-pyran-2-yloxy)-hexahydro-pentalen-1-one

Downstream raw materials:

(1R,3aR,6R,6aR)-(+)-6-(Benzoyloxy)-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(1H)-pentalenon

(-)-Hypnophilin

(3aS,3bR,4R,6aS)-(-)-6-(Benzoyloxy)-3,3a,3b,4,5,6,6a,7-octahydro-3a,5,5-trimethyl-2H-cyclopentapentalen-2-on

(1S,3aR,6R,6aR)-(+)-6-(Benzoyloxy)-1-(2-chlor-2-propenyl)-3,3a,4,5,6,6a-hexahydro-1,5,5-trimethyl-2(1H)-pentalenon