6'-allyloxy-3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-β-D-glucopyranoside

Base Information

Chemical Name:6'-allyloxy-3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-β-D-glucopyranoside
CAS No.:209746-57-6
Molecular Formula:C₂₇H₃₀O₉
Molecular Weight:498.53
Hs Code.:

Synonyms:6'-allyloxy-3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-β-D-glucopyranoside

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Chemical Property of 6'-allyloxy-3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-β-D-glucopyranoside

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Technology Process of 6'-allyloxy-3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-β-D-glucopyranoside

There total 8 articles about 6'-allyloxy-3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-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: 94.0%

: 106-95-6
allyl bromide

: 209746-56-5
3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-β-D-glucopyranoside

: 209746-57-6
6'-allyloxy-3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-β-D-glucopyranoside

Guidance literature:: With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 10h;
DOI:10.1021/jm990175n

Reference yield:

: 504-15-4
orcinol

: 209746-57-6
6'-allyloxy-3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: pyridine

2.1: AlCl₃ / 1.5 h / 145 - 150 °C

3.1: 85 percent aq. H₂SO₄ / 2 h / 20 °C

4.1: 81 percent / benzyltributylammonium chloride; aq. K₂CO₃ / CHCl₃ / 27 h / 20 °C

5.1: 50 percent aq. KOH / ethanol / 0.17 h / 20 °C

5.2: ethanol / 16 h / 20 °C

6.1: 4-(dimethylamino)pyridine / 10 percent Pt/C / ethanol; H₂O / 9 h / 20 °C

7.1: 94 percent / K₂CO₃ / dimethylformamide / 10 h / 20 °C

With pyridine; dmap; potassium hydroxide; aluminium trichloride; sulfuric acid; benzyltri(n-butyl)ammonium chloride; potassium carbonate; platinum on activated charcoal; In ethanol; chloroform; water; N,N-dimethyl-formamide; 1.1: Acetylation / 2.1: Fries rearrangement / 3.1: Deacetylation / 4.1: glycosylation / 5.1: Deacetylation / 5.2: Condensation / 6.1: Catalytic hydrogenation / 7.1: Alkylation;
DOI:10.1021/jm990175n

Reference yield:

: 13444-19-4
2,4-diacetyl-5-methyl-resorcinol

: 209746-57-6
6'-allyloxy-3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 85 percent aq. H₂SO₄ / 2 h / 20 °C

2.1: 81 percent / benzyltributylammonium chloride; aq. K₂CO₃ / CHCl₃ / 27 h / 20 °C

3.1: 50 percent aq. KOH / ethanol / 0.17 h / 20 °C

3.2: ethanol / 16 h / 20 °C

4.1: 4-(dimethylamino)pyridine / 10 percent Pt/C / ethanol; H₂O / 9 h / 20 °C

5.1: 94 percent / K₂CO₃ / dimethylformamide / 10 h / 20 °C

With dmap; potassium hydroxide; sulfuric acid; benzyltri(n-butyl)ammonium chloride; potassium carbonate; platinum on activated charcoal; In ethanol; chloroform; water; N,N-dimethyl-formamide; 1.1: Deacetylation / 2.1: glycosylation / 3.1: Deacetylation / 3.2: Condensation / 4.1: Catalytic hydrogenation / 5.1: Alkylation;
DOI:10.1021/jm990175n