2',6'-dihydroxy-4'methoxymethyloxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside

Base Information

Chemical Name:2',6'-dihydroxy-4'methoxymethyloxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside
CAS No.:257621-38-8
Molecular Formula:C₂₄H₃₀O₁₄
Molecular Weight:542.494
Hs Code.:

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

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

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

There total 5 articles about 2',6'-dihydroxy-4'methoxymethyloxyacetophenone 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: 80.0%

: 257621-57-1
1-(2,6-dihydroxy-4-(methoxymethoxy)phenyl)ethan-1-one

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

: 257621-38-8
2',6'-dihydroxy-4'methoxymethyloxyacetophenone 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:

: 480-66-0,67471-34-5
2,4,6-trihydroxyacetophenone

: 257621-38-8
2',6'-dihydroxy-4'methoxymethyloxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 56 percent / imidazole / dimethylformamide / 24 h / 20 °C

2: 82 percent / pyridine / 1.5 h / 20 °C

3: 83 percent / n-Bu₄NF / tetrahydrofuran / 1.5 h / 20 °C

4: 92 percent / K₂CO₃ / methanol; tetrahydrofuran / 1 h / 20 °C

5: 80 percent / benzyltributylammonium chloride; aq. K₂CO₃ / CHCl₃ / 27 h / 20 °C

With pyridine; 1H-imidazole; tetrabutyl ammonium fluoride; benzyltri(n-butyl)ammonium chloride; potassium carbonate; In tetrahydrofuran; methanol; chloroform; N,N-dimethyl-formamide; 1: triisopropylsilylation / 2: Acylation / 3: Alkylation / 4: Hydrolysis / 5: glycosylation;
DOI:10.1021/jm990175n

Reference yield:

: 257621-45-7
2',6'-dihydroxy-4'-triisopropylsilyloxyacetophenone

: 257621-38-8
2',6'-dihydroxy-4'methoxymethyloxyacetophenone 2'-O-(2,3,4,6-O-tetraacetyl)-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / pyridine / 1.5 h / 20 °C

2: 83 percent / n-Bu₄NF / tetrahydrofuran / 1.5 h / 20 °C

3: 92 percent / K₂CO₃ / methanol; tetrahydrofuran / 1 h / 20 °C

4: 80 percent / benzyltributylammonium chloride; aq. K₂CO₃ / CHCl₃ / 27 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; benzyltri(n-butyl)ammonium chloride; potassium carbonate; In tetrahydrofuran; methanol; chloroform; 1: Acylation / 2: Alkylation / 3: Hydrolysis / 4: glycosylation;
DOI:10.1021/jm990175n