6'-acetoxy-3-(benzo[b]furan-5-yl)-2'-hydroxy-4'-methylpropiophenone 2'-O-(2,3-O-diacetyl-4,6-O-benzylidene-β-D-glucopyranoside)

Base Information

Chemical Name:6'-acetoxy-3-(benzo[b]furan-5-yl)-2'-hydroxy-4'-methylpropiophenone 2'-O-(2,3-O-diacetyl-4,6-O-benzylidene-β-D-glucopyranoside)
CAS No.:209746-80-5
Molecular Formula:C₃₇H₃₆O₁₂
Molecular Weight:672.686
Hs Code.:

Synonyms:6'-acetoxy-3-(benzo[b]furan-5-yl)-2'-hydroxy-4'-methylpropiophenone 2'-O-(2,3-O-diacetyl-4,6-O-benzylidene-β-D-glucopyranoside)

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

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

There total 10 articles about 6'-acetoxy-3-(benzo[b]furan-5-yl)-2'-hydroxy-4'-methylpropiophenone 2'-O-(2,3-O-diacetyl-4,6-O-benzylidene-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: 95.0%

: 108-24-7
acetic anhydride

: 209746-75-8
3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-(4,6-O-benzylidene-β-D-glucopyranoside)

: 209746-80-5
6'-acetoxy-3-(benzo[b]furan-5-yl)-2'-hydroxy-4'-methylpropiophenone 2'-O-(2,3-O-diacetyl-4,6-O-benzylidene-β-D-glucopyranoside)

Guidance literature:: With pyridine; at 20 ℃; for 4.5h;
DOI:10.1021/jm990175n

Reference yield:

: 504-15-4
orcinol

: 209746-80-5
6'-acetoxy-3-(benzo[b]furan-5-yl)-2'-hydroxy-4'-methylpropiophenone 2'-O-(2,3-O-diacetyl-4,6-O-benzylidene-β-D-glucopyranoside)

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: 92 percent / p-TsOH*H₂O / CH₂Cl₂ / 1.5 h / 20 °C

8.1: 95 percent / pyridine / 4.5 h / 20 °C

With pyridine; dmap; potassium hydroxide; aluminium trichloride; sulfuric acid; benzyltri(n-butyl)ammonium chloride; potassium carbonate; toluene-4-sulfonic acid; platinum on activated charcoal; In ethanol; dichloromethane; chloroform; water; 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: benzylidenation / 8.1: Acetylation;
DOI:10.1021/jm990175n

Reference yield:

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

: 209746-80-5
6'-acetoxy-3-(benzo[b]furan-5-yl)-2'-hydroxy-4'-methylpropiophenone 2'-O-(2,3-O-diacetyl-4,6-O-benzylidene-β-D-glucopyranoside)

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: 92 percent / p-TsOH*H₂O / CH₂Cl₂ / 1.5 h / 20 °C

6.1: 95 percent / pyridine / 4.5 h / 20 °C

With pyridine; dmap; potassium hydroxide; sulfuric acid; benzyltri(n-butyl)ammonium chloride; potassium carbonate; toluene-4-sulfonic acid; platinum on activated charcoal; In ethanol; dichloromethane; chloroform; water; 1.1: Deacetylation / 2.1: glycosylation / 3.1: Deacetylation / 3.2: Condensation / 4.1: Catalytic hydrogenation / 5.1: benzylidenation / 6.1: Acetylation;
DOI:10.1021/jm990175n