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

Base Information

• Chemical Name: Acetic acid (1R,3R,4S)-4-acetoxy-3-allyl-2-benzyloxymethyl-cyclopentyl ester
• CAS No.: 76047-68-2
• Molecular Formula: C₂₀H₂₆O₅
• Molecular Weight: 346.423
• Mol file: 76047-68-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about Acetic acid (1R,3R,4S)-4-acetoxy-3-allyl-2-benzyloxymethyl-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:

acetic anhydride (108-24-7) + (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) + Methylenetriphenylphosphorane (19493-09-5) → Acetic acid (1R,3R,4S)-4-acetoxy-3-allyl-2-benzyloxymethyl-cyclopentyl ester (76047-68-2)

Guidance literature:

Yield given. Multistep reaction;

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

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:

Acetic acid (1R,3R,4S)-4-acetoxy-3-allyl-2-benzyloxymethyl-cyclopentyl ester (76047-68-2) → C25H32O6 (76047-76-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 65 percent / N-bromosuccinimide / dimethylsulfoxide; H₂O / 0.5 h / 20 °C

2: pTsOH / CH₂Cl₂ / 25 °C

3: 20 percent KOH / CDCl₃ / 1 h / 60 °C

5: pTsOH / benzene

6: Collons oxidn.

7: 1,2-dimethoxy-ethane / -20 °C

With potassium hydroxide; N-Bromosuccinimide; toluene-4-sulfonic acid; In 1,2-dimethoxyethane; chloroform-d1; dichloromethane; water; dimethyl sulfoxide; benzene;

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

upstream raw materials:

acetic anhydride

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

Methylenetriphenylphosphorane

Downstream raw materials:

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

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

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

C₁₈H₂₂O₆