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

Base Information

Chemical Name:4,4',6'-tri(benzyloxy)-2'-hydroxy-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone
CAS No.:898550-56-6
Molecular Formula:C₇₀H₆₄O₁₀
Molecular Weight:1065.27
Hs Code.:

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

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

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

There total 10 articles about 4,4',6'-tri(benzyloxy)-2'-hydroxy-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone 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: 98.0%

: 4397-53-9
p-benzyloxybenzaldehyde

: 169566-46-5
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

: 898550-56-6
4,4',6'-tri(benzyloxy)-2'-hydroxy-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone

Guidance literature:: With sodium methylate; In 1,4-dioxane; methanol; at 20 ℃; for 20h;
DOI:10.1016/j.carres.2006.03.038

Reference yield:

: 100-39-0
benzyl bromide

: 898550-56-6
4,4',6'-tri(benzyloxy)-2'-hydroxy-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone

Guidance literature:: Multi-step reaction with 3 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 0 °C

1.2: 1 h

2.1: scandium tris(trifluoromethanesulfonate) / 1,2-dichloro-ethane / 5.5 h / -30 - 20 °C

3.1: sodium hydroxide / 1,4-dioxane; water / 24 h / Reflux

With potassium carbonate; sodium hydroxide; scandium tris(trifluoromethanesulfonate); In 1,4-dioxane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/jm501069h

Reference yield:

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

: 898550-56-6
4,4',6'-tri(benzyloxy)-2'-hydroxy-3'-C-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)chalcone

Guidance literature:: Multi-step reaction with 3 steps

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

2.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 0 °C

2.2: 2 h / 20 °C

3.1: sodium hydroxide / 1,4-dioxane; water / 24 h / Reflux

With trimethylsilyl trifluoromethanesulfonate; potassium carbonate; sodium hydroxide; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jm501069h