4,6-bis-hydroxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-hydroxyacetophenone

Base Information

• Chemical Name: 4,6-bis-hydroxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-hydroxyacetophenone
• CAS No.: 1309438-45-6
• Molecular Formula: C₄₂H₄₂O₉
• Molecular Weight: 690.79
• Mol file: 1309438-45-6.mol

Synonyms:4,6-bis-hydroxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-hydroxyacetophenone

Chemical Property of 4,6-bis-hydroxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-hydroxyacetophenone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4,6-bis-hydroxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-hydroxyacetophenone

There total 7 articles about 4,6-bis-hydroxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-hydroxyacetophenone 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: 57.0%

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) + 2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5) → 4,6-bis-hydroxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-hydroxyacetophenone (1309438-45-6)

Guidance literature:

With calcium sulfate; trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile;

DOI:10.1021/acs.jmedchem.0c00841

Reference yield: 48.0%

2,4,6-trihydroxyacetophenone (480-66-0,67471-34-5) + 2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate (132201-75-3) → 4,6-bis-hydroxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-hydroxyacetophenone (1309438-45-6)

Guidance literature:

2,4,6-trihydroxyacetophenone; 2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate; With boron trifluoride diethyl etherate; In tetrahydrofuran; dichloromethane; at -78 - 55 ℃; for 9h;

With sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; water; for 0.0833333h;

Reference yield:

benzyl bromide (100-39-0) → 4,6-bis-hydroxy-3-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2-hydroxyacetophenone (1309438-45-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C

1.2: 24 h / 20 °C

2.1: acetic acid; sulfuric acid / 24 h / 90 - 95 °C

3.1: trimethylsilyl trifluoromethanesulfonate / acetonitrile; dichloromethane / 3.5 h / -40 - 20 °C / Inert atmosphere

With trimethylsilyl trifluoromethanesulfonate; sulfuric acid; sodium hydride; acetic acid; In dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;

DOI:10.1021/jm501069h

upstream raw materials:

2,4,6-trihydroxyacetophenone

2,3,4,6-tetra-O-benzyl-D-glucopyranose trichloroacetimidate

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

benzyl bromide

Downstream raw materials:

(2E)-1-[2-acetoxy-4,6-dibenzyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)]phenyl-3-(4-benzyloxyphenyl)prop-2-en-1-one

4,4',6'-tri(benzyloxy)-2'-hydroxy-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone

1-(4,6-bis(benzyloxy)-2-hydroxy-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran-2-yl)phenyl)ethanone

3′-glucosyl-2′,4′,6′-trihydroxyacetophenone