3α-hydroxy-4β-bromo-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane benzoate

Base Information

• Chemical Name: 3α-hydroxy-4β-bromo-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane benzoate
• CAS No.: 82259-29-8
• Molecular Formula: C₂₃H₂₃BrO₄
• Molecular Weight: 443.337
• Mol file: 82259-29-8.mol

Synonyms:3α-hydroxy-4β-bromo-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane benzoate

Chemical Property of 3α-hydroxy-4β-bromo-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3α-hydroxy-4β-bromo-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane benzoate

There total 5 articles about 3α-hydroxy-4β-bromo-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane benzoate 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: 93.0%

3α-hydroxy-4β-bromo-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane (73996-36-8) + benzoyl chloride (98-88-4) → 3α-hydroxy-4β-bromo-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane benzoate (82259-29-8)

Guidance literature:

In pyridine; dichloromethane; for 16h; Ambient temperature;

DOI:10.1016/0040-4020(81)80005-1

Reference yield:

7-oxo-2β-benzyloxymethyl-3-bicyclo<3.3.0>octene (73995-74-1) → 3α-hydroxy-4β-bromo-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane benzoate (82259-29-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / N-bromosuccinimide / dimethylsulfoxide; H₂O / 15 deg C (adding), then RT, 30 min

2: 93 percent / pyridine; CH₂Cl₂ / 16 h / Ambient temperature

With N-Bromosuccinimide; In pyridine; dichloromethane; water; dimethyl sulfoxide;

DOI:10.1016/0040-4020(81)80005-1

Reference yield:

3α-hydroxy-2β-(benzyloxymethyl)-4-cyclopentene-1α-acetic acid (41787-51-3) → 3α-hydroxy-4β-bromo-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane benzoate (82259-29-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / K₂CO₃ / acetone / 16 h / 35 °C

2: 57 percent / hydroquinone / 12 h / 140 °C

3: 1.) potassium t-butoxide, 2.) NaCl / 1.) benzene, 50 deg C (adding), then 65 deg C, 1.5 h, 2.) DMSO-H₂O, 120 deg C, 1.5 h

4: 77 percent / N-bromosuccinimide / dimethylsulfoxide; H₂O / 15 deg C (adding), then RT, 30 min

5: 93 percent / pyridine; CH₂Cl₂ / 16 h / Ambient temperature

With N-Bromosuccinimide; potassium tert-butylate; potassium carbonate; hydroquinone; sodium chloride; In pyridine; dichloromethane; water; dimethyl sulfoxide; acetone;

DOI:10.1016/0040-4020(81)80005-1

upstream raw materials:

3α-hydroxy-4β-bromo-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane

benzoyl chloride

7-oxo-2β-benzyloxymethyl-3-bicyclo<3.3.0>octene

methyl 2β-(benzyloxymethyl)-5α-(carboethoxymethyl)-3-cyclopentene-1α-acetate