3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4',7-di-O-benzyl-3',5-dihydroxyflavonol

Base Information

• Chemical Name: 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4',7-di-O-benzyl-3',5-dihydroxyflavonol
• CAS No.: 131021-81-3
• Molecular Formula: C₄₃H₄₀O₁₆
• Molecular Weight: 812.781
• Mol file: 131021-81-3.mol

Synonyms:3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4',7-di-O-benzyl-3',5-dihydroxyflavonol

Chemical Property of 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4',7-di-O-benzyl-3',5-dihydroxyflavonol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4',7-di-O-benzyl-3',5-dihydroxyflavonol

There total 9 articles about 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4',7-di-O-benzyl-3',5-dihydroxyflavonol 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: 61.0%

benzyl bromide (100-39-0) + 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-3',4',5,7-tetrahydroxyflavonol (39028-59-6) → 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4',7-di-O-benzyl-3',5-dihydroxyflavonol (131021-81-3)

Guidance literature:

3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-3',4',5,7-tetrahydroxyflavonol; With potassium carbonate; In N,N-dimethyl-formamide; at 0 ℃; for 0.0833333h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; at 0 ℃; for 12h; Inert atmosphere;

DOI:10.1021/acs.jnatprod.6b00274

Reference yield: 56.0%

7,4’-di-O-benzylquercetin (13459-13-7) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4',7-di-O-benzyl-3',5-dihydroxyflavonol (131021-81-3)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 32h; Inert atmosphere;

DOI:10.1080/07328303.2011.616979

Reference yield:

quercetol (117-39-5,74893-81-5) → 3-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)-4',7-di-O-benzyl-3',5-dihydroxyflavonol (131021-81-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: pyridine / 4 h / 140 - 145 °C

2.1: potassium carbonate; potassium iodide / acetone / 120 h / Heating

3.1: sodium hydroxide / water; acetone / 3 h / 0 °C / Inert atmosphere

3.2: 0.5 h / 0 °C / Inert atmosphere

4.1: potassium carbonate / N,N-dimethyl-formamide / 32 h / 20 °C / Inert atmosphere

With pyridine; potassium carbonate; potassium iodide; sodium hydroxide; In water; N,N-dimethyl-formamide; acetone;

DOI:10.1080/07328303.2011.616979

upstream raw materials:

7,4’-di-O-benzylquercetin

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

quercetol

3,5,7-triacetoxy-2-(3,4-diacetoxy-phenyl)-chromen-4-one

Downstream raw materials:

isoquercetin

4',7-di-O-benzyl-3-O-(β-D-glucopyranosyl)quercetin

Apigen-4'7-diyl-di(2,3,4,6-tetra-O-acetyl-β-D-glucopranoside)

Refernces

• 1、 Ren, Xuhong,Shen, Liu-Lan,Muraoka, Osamu,Cheng, Maosheng. "Synthesis of quercetin 3-O-[6"-O-(trans-p-coumaroyl)]-β-D- Glucopyranoside". experimental part. p. 119 - 131. Retrieved 2012/01/13.