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

Base Information

• Chemical Name: 3-(benzo[b]furan-5-yl)-6'-tert-butyldimethylsilyloxy-2'-hydroxy-4'-methylpropiophenone 2'-O-(4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside)
• CAS No.: 209746-76-9
• Molecular Formula: C₄₃H₅₈O₉Si₂
• Molecular Weight: 775.099

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

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

Chemical Property:

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

There total 9 articles about 3-(benzo[b]furan-5-yl)-6'-tert-butyldimethylsilyloxy-2'-hydroxy-4'-methylpropiophenone 2'-O-(4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-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: 75.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 3-(benzo[b]furan-5-yl)-2',6'-dihydroxy-4'-methylpropiophenone 2'-O-(4,6-O-benzylidene-β-D-glucopyranoside) (209746-75-8) → 3-(benzo[b]furan-5-yl)-6'-tert-butyldimethylsilyloxy-2'-hydroxy-4'-methylpropiophenone 2'-O-(4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside) (209746-76-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 13h;

DOI:10.1021/jm990175n

Reference yield:

orcinol (504-15-4) → 3-(benzo[b]furan-5-yl)-6'-tert-butyldimethylsilyloxy-2'-hydroxy-4'-methylpropiophenone 2'-O-(4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside) (209746-76-9)

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: 75 percent / imidazole / dimethylformamide / 13 h / 20 °C

With pyridine; 1H-imidazole; 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; 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: benzylidenation / 8.1: bissilylation;

DOI:10.1021/jm990175n

Reference yield:

2,4-diacetyl-5-methyl-resorcinol (13444-19-4) → 3-(benzo[b]furan-5-yl)-6'-tert-butyldimethylsilyloxy-2'-hydroxy-4'-methylpropiophenone 2'-O-(4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside) (209746-76-9)

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: 75 percent / imidazole / dimethylformamide / 13 h / 20 °C

With 1H-imidazole; 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; N,N-dimethyl-formamide; 1.1: Deacetylation / 2.1: glycosylation / 3.1: Deacetylation / 3.2: Condensation / 4.1: Catalytic hydrogenation / 5.1: benzylidenation / 6.1: bissilylation;

DOI:10.1021/jm990175n

upstream raw materials:

tert-butyldimethylsilyl chloride

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

orcinol

2,4-diacetyl-5-methyl-resorcinol

Downstream raw materials:

3-(benzo[b]furan-5-yl)-6'-tert-butyldimethylsilyloxy-2'-hydroxy-4'-methylpropiophenone 2'-O-(2-O-acetyl-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-β-D-glucopyranoside)

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