3-Benzofuran-5-yl-1-[2-methoxymethoxy-6-((2S,3S,4R,5R,6R)-3,4,5-tris-methoxymethoxy-6-methoxymethoxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propan-1-one

Base Information

• Chemical Name: 3-Benzofuran-5-yl-1-[2-methoxymethoxy-6-((2S,3S,4R,5R,6R)-3,4,5-tris-methoxymethoxy-6-methoxymethoxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propan-1-one
• CAS No.: 320372-08-5
• Molecular Formula: C₃₄H₄₆O₁₃
• Molecular Weight: 662.731

Synonyms:3-Benzofuran-5-yl-1-[2-methoxymethoxy-6-((2S,3S,4R,5R,6R)-3,4,5-tris-methoxymethoxy-6-methoxymethoxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propan-1-one

Chemical Property of 3-Benzofuran-5-yl-1-[2-methoxymethoxy-6-((2S,3S,4R,5R,6R)-3,4,5-tris-methoxymethoxy-6-methoxymethoxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propan-1-one

Chemical Property:

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Technology Process of 3-Benzofuran-5-yl-1-[2-methoxymethoxy-6-((2S,3S,4R,5R,6R)-3,4,5-tris-methoxymethoxy-6-methoxymethoxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propan-1-one

There total 5 articles about 3-Benzofuran-5-yl-1-[2-methoxymethoxy-6-((2S,3S,4R,5R,6R)-3,4,5-tris-methoxymethoxy-6-methoxymethoxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propan-1-one 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: 50.0%

(2R,3R,4S,5R)-3,4,5-tris(methoxymethoxy)-2-((methoxymethoxy)methyl)-6-methylenetetrahydro-2H-pyran (189825-52-3) + trifluoro-methanesulfonic acid 2-(3-benzofuran-5-yl-propionyl)-3-methoxymethoxy-phenyl ester (320371-86-6) → 3-Benzofuran-5-yl-1-[2-methoxymethoxy-6-((2S,3S,4R,5R,6R)-3,4,5-tris-methoxymethoxy-6-methoxymethoxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propan-1-one (320372-08-5) + 3-Benzofuran-5-yl-1-[2-((3S,4R,5R,6R)-6-hydroxy-3,4,5,7-tetrakis-methoxymethoxy-heptyl)-6-methoxymethoxy-phenyl]-propan-1-one

Guidance literature:

(2R,3R,4S,5R)-3,4,5-tris(methoxymethoxy)-2-((methoxymethoxy)methyl)-6-methylenetetrahydro-2H-pyran; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; Heating;

trifluoro-methanesulfonic acid 2-(3-benzofuran-5-yl-propionyl)-3-methoxymethoxy-phenyl ester; With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In water; N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1016/S0040-4039(00)01709-3

Reference yield:

2,6-dihydroxylacetophenone (699-83-2) → 3-Benzofuran-5-yl-1-[2-methoxymethoxy-6-((2S,3S,4R,5R,6R)-3,4,5-tris-methoxymethoxy-6-methoxymethoxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propan-1-one (320372-08-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 20 °C

1.2: 60 percent / dimethylformamide / 20 °C

2.1: 82 percent / KOH / ethanol / 20 °C

3.1: 50 percent / H₂ / Rh(PPh₃)3Cl / benzene / 80 °C / 3040 Torr

4.1: 96 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

5.1: 9-BBN / tetrahydrofuran / Heating

5.2: 50 percent / K₃PO₄ / Pd(dppf)*CH₂Cl₂ / H₂O; dimethylformamide / 18 h / 20 °C

With potassium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; sodium hydride; N-ethyl-N,N-diisopropylamine; Wilkinson's catalyst; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; benzene; 5.2: Suzuki coupling;

DOI:10.1016/S0040-4039(00)01709-3

Reference yield:

2′-hydroxy-6′-methoxymethoxyacetophenone (78646-28-3) → 3-Benzofuran-5-yl-1-[2-methoxymethoxy-6-((2S,3S,4R,5R,6R)-3,4,5-tris-methoxymethoxy-6-methoxymethoxymethyl-tetrahydro-pyran-2-ylmethyl)-phenyl]-propan-1-one (320372-08-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 82 percent / KOH / ethanol / 20 °C

2.1: 50 percent / H₂ / Rh(PPh₃)3Cl / benzene / 80 °C / 3040 Torr

3.1: 96 percent / i-Pr₂NEt / CH₂Cl₂ / 20 °C

4.1: 9-BBN / tetrahydrofuran / Heating

4.2: 50 percent / K₃PO₄ / Pd(dppf)*CH₂Cl₂ / H₂O; dimethylformamide / 18 h / 20 °C

With potassium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; N-ethyl-N,N-diisopropylamine; Wilkinson's catalyst; In tetrahydrofuran; ethanol; dichloromethane; benzene; 4.2: Suzuki coupling;

DOI:10.1016/S0040-4039(00)01709-3

upstream raw materials:

(2R,3R,4S,5R)-3,4,5-tris(methoxymethoxy)-2-((methoxymethoxy)methyl)-6-methylenetetrahydro-2H-pyran

trifluoro-methanesulfonic acid 2-(3-benzofuran-5-yl-propionyl)-3-methoxymethoxy-phenyl ester

2,6-dihydroxylacetophenone

2′-hydroxy-6′-methoxymethoxyacetophenone

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