Acetic acid (1S,2R,4R)-4-acetoxy-3-benzyloxymethyl-2-(3-bromo-2-hydroxy-propyl)-cyclopentyl ester

Base Information

• Chemical Name: Acetic acid (1S,2R,4R)-4-acetoxy-3-benzyloxymethyl-2-(3-bromo-2-hydroxy-propyl)-cyclopentyl ester
• CAS No.: 76047-69-3
• Molecular Formula: C₂₀H₂₇BrO₆
• Molecular Weight: 443.335

Synonyms:Acetic acid (1S,2R,4R)-4-acetoxy-3-benzyloxymethyl-2-(3-bromo-2-hydroxy-propyl)-cyclopentyl ester

Chemical Property of Acetic acid (1S,2R,4R)-4-acetoxy-3-benzyloxymethyl-2-(3-bromo-2-hydroxy-propyl)-cyclopentyl ester

Chemical Property:

Purity/Quality:

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Technology Process of Acetic acid (1S,2R,4R)-4-acetoxy-3-benzyloxymethyl-2-(3-bromo-2-hydroxy-propyl)-cyclopentyl ester

There total 2 articles about Acetic acid (1S,2R,4R)-4-acetoxy-3-benzyloxymethyl-2-(3-bromo-2-hydroxy-propyl)-cyclopentyl ester 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: 20.0%

Acetic acid (1R,3R,4S)-4-acetoxy-3-allyl-2-benzyloxymethyl-cyclopentyl ester (76047-68-2) → Acetic acid (1S,2R,4R)-4-acetoxy-3-benzyloxymethyl-2-(2-bromo-3-hydroxy-propyl)-cyclopentyl ester (76047-70-6) + Acetic acid (1S,2R,4R)-4-acetoxy-3-benzyloxymethyl-2-(3-bromo-2-hydroxy-propyl)-cyclopentyl ester (76047-69-3)

Guidance literature:

With N-Bromosuccinimide; In water; dimethyl sulfoxide; at 20 ℃; for 0.5h;

DOI:10.1016/S0040-4039(00)78662-X

Reference yield:

(3aR,5R,6aS)-4-Benzyloxymethyl-5-hydroxy-hexahydro-cyclopenta[b]furan-2-one (35733-59-6,38931-62-3,42586-91-4,42586-93-6,72777-82-3,119817-19-5) → Acetic acid (1S,2R,4R)-4-acetoxy-3-benzyloxymethyl-2-(3-bromo-2-hydroxy-propyl)-cyclopentyl ester (76047-69-3)

Guidance literature:

Multi-step reaction with 2 steps

2: 65 percent / N-bromosuccinimide / dimethylsulfoxide; H₂O / 0.5 h / 20 °C

With N-Bromosuccinimide; In water; dimethyl sulfoxide;

DOI:10.1016/S0040-4039(00)78662-X

Reference yield:

3,4-dihydro-2H-pyran (110-87-2) + Acetic acid (1S,2R,4R)-4-acetoxy-3-benzyloxymethyl-2-(3-bromo-2-hydroxy-propyl)-cyclopentyl ester (76047-69-3) → Acetic acid (1S,2R,4R)-4-acetoxy-3-benzyloxymethyl-2-[3-bromo-2-(tetrahydro-pyran-4-yloxy)-propyl]-cyclopentyl ester

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 25 ℃;

DOI:10.1016/S0040-4039(00)78662-X

upstream raw materials:

Acetic acid (1R,3R,4S)-4-acetoxy-3-allyl-2-benzyloxymethyl-cyclopentyl ester

(3aR,5R,6aS)-4-Benzyloxymethyl-5-hydroxy-hexahydro-cyclopenta[b]furan-2-one

Downstream raw materials:

Benzoic acid (4aR,6R,7aS)-5-hydroxymethyl-3-oxo-octahydro-cyclopenta[b]pyran-6-yl ester

C₁₈H₂₂O₆

C₁₈H₂₀O₆

C₂₅H₃₂O₆

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