3-(5-benzo[b]furanyl)-2'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone

Base Information

Chemical Name:3-(5-benzo[b]furanyl)-2'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone
CAS No.:209746-58-7
Molecular Formula:C₂₉H₃₂O₁₁
Molecular Weight:556.566
Hs Code.:

Synonyms:3-(5-benzo[b]furanyl)-2'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of 3-(5-benzo[b]furanyl)-2'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of 3-(5-benzo[b]furanyl)-2'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone

There total 9 articles about 3-(5-benzo[b]furanyl)-2'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone 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: 87.0%

: 79-22-1
methyl chloroformate

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

: 209746-58-7
3-(5-benzo[b]furanyl)-2'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone

Guidance literature:: With 2,4,6-trimethyl-pyridine; In dichloromethane; at -40 - 20 ℃; for 2.5h;
DOI:10.1021/jm990175n

Reference yield:

: 504-15-4
orcinol

: 209746-58-7
3-(5-benzo[b]furanyl)-2'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone

Guidance literature:: Multi-step reaction with 8 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

8.1: 87 percent / 2,4,6-collidine / CH₂Cl₂ / 2.5 h / -40 - 20 °C

With pyridine; 2,4,6-trimethyl-pyridine; dmap; potassium hydroxide; aluminium trichloride; sulfuric acid; benzyltri(n-butyl)ammonium chloride; potassium carbonate; platinum on activated charcoal; In ethanol; dichloromethane; 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 / 8.1: Acylation;
DOI:10.1021/jm990175n

Reference yield:

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

: 209746-58-7
3-(5-benzo[b]furanyl)-2'-(6-O-methoxycarbonyl-β-D-glucopyranosyloxy)-6'-allyloxy-4'-methylpropiophenone

Guidance literature:: Multi-step reaction with 6 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

6.1: 87 percent / 2,4,6-collidine / CH₂Cl₂ / 2.5 h / -40 - 20 °C

With 2,4,6-trimethyl-pyridine; dmap; potassium hydroxide; sulfuric acid; benzyltri(n-butyl)ammonium chloride; potassium carbonate; platinum on activated charcoal; In ethanol; dichloromethane; 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 / 6.1: Acylation;
DOI:10.1021/jm990175n