(2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine

Base Information

• Chemical Name: (2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine
• CAS No.: 933992-79-1
• Molecular Formula: C₂₁H₂₅NO₄
• Molecular Weight: 355.434
• Mol file: 933992-79-1.mol

Synonyms:(2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine

Chemical Property of (2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine

There total 12 articles about (2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine 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: 89.0%

(-)-anisomycin (22862-76-6) + benzyl bromide (100-39-0) → (2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine (933992-79-1)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1039/b616494c

Reference yield:

benzyl bromide (100-39-0) → (2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine (933992-79-1)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / CHCl₃ / 2 h

2: CHCl₃ / 5 h / 60 °C

3: HCl, water / palladium-charcoal 10percent / methanol / 48 h / Heating

With hydrogenchloride; water; triethylamine; palladium on activated charcoal; In methanol; chloroform;

DOI:10.1039/P19850001463

Reference yield:

(2R,3S,4S)-4-allyloxy-3-hydroxy-2-(p-methoxybenzyl)-pyrrolidine (87796-46-1) → (2R,3S,4S)-3-acetoxy-1-benzyl-4-hydroxy-2-(4-methoxybenzyl)-pyrrolidine (933992-79-1)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine / CHCl₃ / 2 h

2: CHCl₃ / 5 h / 60 °C

3: HCl, water / palladium-charcoal 10percent / methanol / 48 h / Heating

With hydrogenchloride; water; triethylamine; palladium on activated charcoal; In methanol; chloroform;

DOI:10.1039/P19850001463

upstream raw materials:

(2R,3S,4S)-3-acetoxy-4-allyloxy-1-benzyl-2-(p-methoxybenzyl)pyrrolidine

(-)-anisomycin

benzyl bromide

(2R,3S,4S)-4-allyloxy-3-hydroxy-2-(p-methoxybenzyl)-pyrrolidine

Downstream raw materials:

(-)-anisomycin

Refernces

• 1、 Buchanan, J. Grant,MacLean, Keith A.,Wightman, Richard H.,Paulsen, Hans. "A New Synthesis of (-)-Anisomycin and its Demethoxy analogue from D-Ribose". . p. 1463 - 1470. Retrieved 2007/10/02.