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

Base Information

• Chemical Name: 3α-hydroxy-4β-bromo-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane
• CAS No.: 73996-36-8
• Molecular Formula: C₁₆H₁₉BrO₃
• Molecular Weight: 339.229
• Mol file: 73996-36-8.mol

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

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

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

There total 5 articles about 3α-hydroxy-4β-bromo-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane 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: 77.0%

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 (73996-36-8)

Guidance literature:

With N-Bromosuccinimide; In water; dimethyl sulfoxide; 15 deg C (adding), then RT, 30 min;

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

Reference yield:

methyl 2β-(benzyloxymethyl)-5α-(carboethoxymethyl)-3-cyclopentene-1α-acetate (73995-77-4) → 3α-hydroxy-4β-bromo-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane (73996-36-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 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

2: 77 percent / N-bromosuccinimide / dimethylsulfoxide; H₂O / 15 deg C (adding), then RT, 30 min

With N-Bromosuccinimide; potassium tert-butylate; sodium chloride; In water; dimethyl sulfoxide;

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

Reference yield:

methyl 3α-hydroxy-2β-(benzyloxymethyl)-4-cyclopentene-1α-acetate (53539-02-9) → 3α-hydroxy-4β-bromo-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane (73996-36-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 57 percent / hydroquinone / 12 h / 140 °C

2: 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

3: 77 percent / N-bromosuccinimide / dimethylsulfoxide; H₂O / 15 deg C (adding), then RT, 30 min

With N-Bromosuccinimide; potassium tert-butylate; hydroquinone; sodium chloride; In water; dimethyl sulfoxide;

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

upstream raw materials:

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

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

methyl 3α-hydroxy-2β-(benzyloxymethyl)-4-cyclopentene-1α-acetate

3α-hydroxy-2β-(benzyloxymethyl)-4-cyclopentene-1α-acetic acid

Downstream raw materials:

3α-hydroxy-7-oxo-2β-benzyloxymethylbicyclo<3.3.0>octane tetrahydropyranyl ether (α-isomer)

carbacyclin

(5E)-6a-carbaprostaglandin I₂ methyl ester

(5E)-carba-PGI2