(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[4-(benzyloxy)phenyl]pyrrolidine

Base Information

• Chemical Name: (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[4-(benzyloxy)phenyl]pyrrolidine
• CAS No.: 1000612-76-9
• Molecular Formula: C₃₉H₃₉NO₅
• Molecular Weight: 601.742
• Mol file: 1000612-76-9.mol

Synonyms:(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[4-(benzyloxy)phenyl]pyrrolidine

Chemical Property of (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[4-(benzyloxy)phenyl]pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[4-(benzyloxy)phenyl]pyrrolidine

There total 2 articles about (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[4-(benzyloxy)phenyl]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: 92.0%

(4-(benzyloxy)phenyl)magnesium bromide (120186-59-6) + (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide (537030-19-6) → (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[4-(benzyloxy)phenyl]pyrrolidine (1000612-76-9)

Guidance literature:

In tetrahydrofuran; at 0 ℃;

DOI:10.1055/s-2007-991059

Reference yield:

p-benzyloxyphenylbromide (6793-92-6) + (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide (537030-19-6) → (2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[4-(benzyloxy)phenyl]pyrrolidine (1000612-76-9)

Guidance literature:

p-benzyloxyphenylbromide; With magnesium; In tetrahydrofuran; Reflux;

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide; In tetrahydrofuran; at 0 ℃;

DOI:10.1016/j.bmc.2008.10.063

Reference yield:

(2R,3R,4R,5R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[4-(benzyloxy)phenyl]pyrrolidine (1000612-76-9) → (2R,3R,4R,5R)-4-(hydroxy)-2-(hydroxymethyl)-5-(4-hydroxyphenyl)pyrrolidin-3-ol (188744-98-1,431981-75-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂; HCl / Pd(OH)2/C / methanol / 20 °C / 3800.26 Torr

2: 99 percent / Dowex 5WX₈-200; aq. NH₄OH

With hydrogenchloride; ammonium hydroxide; hydrogen; palladium dihydroxide; In methanol;

DOI:10.1055/s-2007-991059

upstream raw materials:

(4-(benzyloxy)phenyl)magnesium bromide

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide

p-benzyloxyphenylbromide

Downstream raw materials:

(2R,3R,4R,5R)-4-(hydroxy)-2-(hydroxymethyl)-5-(4-hydroxyphenyl)pyrrolidin-3-ol