3’,4’,5,7-tetra-O-benzyl-8-bromocatechin-(4α8)-3’,4’,5,7-tetra-O-benzylcatechin

Base Information

• Chemical Name: 3’,4’,5,7-tetra-O-benzyl-8-bromocatechin-(4α8)-3’,4’,5,7-tetra-O-benzylcatechin
• CAS No.: 923565-04-2
• Molecular Formula: C₈₆H₇₃BrO₁₂
• Molecular Weight: 1378.42
• Mol file: 923565-04-2.mol

Synonyms:3’,4’,5,7-tetra-O-benzyl-8-bromocatechin-(4α8)-3’,4’,5,7-tetra-O-benzylcatechin

Chemical Property of 3’,4’,5,7-tetra-O-benzyl-8-bromocatechin-(4α8)-3’,4’,5,7-tetra-O-benzylcatechin

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3’,4’,5,7-tetra-O-benzyl-8-bromocatechin-(4α8)-3’,4’,5,7-tetra-O-benzylcatechin

There total 7 articles about 3’,4’,5,7-tetra-O-benzyl-8-bromocatechin-(4α8)-3’,4’,5,7-tetra-O-benzylcatechin 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: 80.0%

3’,4’,5,7-tetra-O-benzyl-4β-(2-hydroxyethyloxy)-8-bromocatechin (923565-00-8) + 5,7,3',4'-tetra-O-benzyl-(+)-catechin (20728-73-8) → 3’,4’,5,7-tetra-O-benzyl-8-bromocatechin-(4α8)-3’,4’,5,7-tetra-O-benzylcatechin (923565-04-2)

Guidance literature:

With sodium tetrachloroaurate(III) dihyrate; In dichloromethane; at 20 ℃; for 4h; Reagent/catalyst; regioselective reaction; Catalytic behavior; Inert atmosphere;

DOI:10.1016/j.tet.2014.11.011

Reference yield: 74.0%

3’,4’,5,7-tetra-O-benzyl-4β-O-propargyl-8-bromocatechin + 5,7,3',4'-tetra-O-benzyl-(+)-catechin (20728-73-8) → 3’,4’,5,7-tetra-O-benzyl-8-bromocatechin-(4α8)-3’,4’,5,7-tetra-O-benzylcatechin (923565-04-2)

Guidance literature:

With iron(III) chloride; In dichloromethane; at 20 ℃; for 4h; Reagent/catalyst; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2014.11.011

Reference yield:

benzyl bromide (100-39-0) → 3’,4’,5,7-tetra-O-benzyl-8-bromocatechin-(4α8)-3’,4’,5,7-tetra-O-benzylcatechin (923565-04-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 81 percent / K₂CO₃ / dimethylformamide / 0 - 20 °C

2: 67 percent / TiCl₄ / CH₂Cl₂ / 3 h / 20 °C / pH 13

With titanium tetrachloride; potassium carbonate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200600668

upstream raw materials:

3’,4’,5,7-tetra-O-benzyl-4β-(2-hydroxyethyloxy)-8-bromocatechin

5,7,3',4'-tetra-O-benzyl-(+)-catechin

benzyl bromide

5,7,3',4'-tetra-O-benzyl-8-bromocatechin

Downstream raw materials:

procyanidin B₃

3,4-cis-(+)-catechin-(4β->8)-(+)-catechin