4'-chloro-2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside

Base Information

Chemical Name:4'-chloro-2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside
CAS No.:257621-36-6
Molecular Formula:C₂₂H₂₅ClO₁₂
Molecular Weight:516.886
Hs Code.:

Synonyms:4'-chloro-2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside

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Chemical Property of 4'-chloro-2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside

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Technology Process of 4'-chloro-2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside

There total 5 articles about 4'-chloro-2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside 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: 48.0%

: 257621-56-0
4'-chloro-2',6'-dihydroxyacetophenone

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: 257621-36-6
4'-chloro-2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside

Guidance literature:: With benzyltri(n-butyl)ammonium chloride; potassium carbonate; In chloroform; at 20 ℃; for 27h;
DOI:10.1021/jm990175n

Reference yield:

: 52780-23-1
chloro-3,5-dihydroxybenzene

: 257621-36-6
4'-chloro-2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: pyridine

2: AlCl₃ / chlorobenzene / 90 °C

3: benzyltributylammonium chloride; aq. K₂CO₃ / CHCl₃

With pyridine; aluminium trichloride; benzyltri(n-butyl)ammonium chloride; potassium carbonate; In chloroform; chlorobenzene; 2: Fries rearrangement;
DOI:10.1016/j.bmcl.2004.07.082

Reference yield:

: 5-chlororesorcinol diacetate

: 257621-36-6
4'-chloro-2',6'-dihydroxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: AlCl₃ / 1.5 h / 145 - 150 °C

2: 85 percent aq. H₂SO₄ / 2 h / 20 °C

3: 48 percent / benzyltributylammonium chloride; aq. K₂CO₃ / CHCl₃ / 27 h / 20 °C

With aluminium trichloride; sulfuric acid; benzyltri(n-butyl)ammonium chloride; potassium carbonate; In chloroform; 1: Fries rearrangement / 2: Deacetylation / 3: glycosylation;
DOI:10.1021/jm990175n