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

Base Information

• Chemical Name: 3α-hydroxy-2β-(benzyloxymethyl)-4-cyclopentene-1α-acetic acid
• CAS No.: 41787-51-3
• Molecular Formula: C₁₅H₁₈O₄
• Molecular Weight: 262.306
• Mol file: 41787-51-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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MSDS Files:

Useful:

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

There total 1 articles about 3α-hydroxy-2β-(benzyloxymethyl)-4-cyclopentene-1α-acetic acid 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:

→ 3α-hydroxy-2β-(benzyloxymethyl)-4-cyclopentene-1α-acetic acid (41787-51-3)

Guidance literature:

bicycl. Keton I, 1. m-Chlorperbenzoesaeure, NaHCO3, 2. OH^-;

DOI:10.1021/ja00735a032

Reference yield: 99.0%

3α-hydroxy-2β-(benzyloxymethyl)-4-cyclopentene-1α-acetic acid (41787-51-3) + methyl iodide (74-88-4) → methyl 3α-hydroxy-2β-(benzyloxymethyl)-4-cyclopentene-1α-acetate (53539-02-9)

Guidance literature:

With potassium carbonate; In acetone; at 35 ℃; for 16h;

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

Downstream raw materials:

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

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

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

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