(E)-3-{4-[2-Acetoxy-2-(4-acetoxy-3-methoxy-phenyl)-1-acetoxymethyl-ethoxy]-3-methoxy-phenyl}-acrylic acid (2S,3S,4R,5R)-3,4-diacetoxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

Base Information

• Chemical Name: (E)-3-{4-[2-Acetoxy-2-(4-acetoxy-3-methoxy-phenyl)-1-acetoxymethyl-ethoxy]-3-methoxy-phenyl}-acrylic acid (2S,3S,4R,5R)-3,4-diacetoxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester
• CAS No.: 146252-15-5
• Molecular Formula: C₃₆H₄₂O₁₇
• Molecular Weight: 746.719

Synonyms:

Chemical Property of (E)-3-{4-[2-Acetoxy-2-(4-acetoxy-3-methoxy-phenyl)-1-acetoxymethyl-ethoxy]-3-methoxy-phenyl}-acrylic acid (2S,3S,4R,5R)-3,4-diacetoxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

Chemical Property:

Purity/Quality:

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Useful:

Technology Process of (E)-3-{4-[2-Acetoxy-2-(4-acetoxy-3-methoxy-phenyl)-1-acetoxymethyl-ethoxy]-3-methoxy-phenyl}-acrylic acid (2S,3S,4R,5R)-3,4-diacetoxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester

There total 10 articles about (E)-3-{4-[2-Acetoxy-2-(4-acetoxy-3-methoxy-phenyl)-1-acetoxymethyl-ethoxy]-3-methoxy-phenyl}-acrylic acid (2S,3S,4R,5R)-3,4-diacetoxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester 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:

4-acetoxy-β-bromo-3-methoxyacetophenone (50893-83-9) → (E)-3-{4-[2-Acetoxy-2-(4-acetoxy-3-methoxy-phenyl)-1-acetoxymethyl-ethoxy]-3-methoxy-phenyl}-acrylic acid (2S,3S,4R,5R)-3,4-diacetoxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester (146252-15-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / K₂CO₃ / acetone / 3 h / Heating

2: 82 percent / K₂CO₃ / dioxane; H₂O / 4 h

3: 94 percent / Zn(BH₄)2 / ethyl acetate; diethyl ether / 0.5 h / 0 °C

With zinc(II) tetrahydroborate; potassium carbonate; In 1,4-dioxane; diethyl ether; water; ethyl acetate; acetone;

DOI:10.1039/P19920002971

Reference yield:

4-acetoxy-β-bromo-3-methoxyacetophenone (50893-83-9) → (E)-3-{4-[2-Acetoxy-2-(4-acetoxy-3-methoxy-phenyl)-1-acetoxymethyl-ethoxy]-3-methoxy-phenyl}-acrylic acid (2S,3S,4R,5R)-3,4-diacetoxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester (146252-15-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / K₂CO₃ / acetone / 3 h / Heating

2: 82 percent / K₂CO₃ / dioxane; H₂O / 4 h

3: 94 percent / Zn(BH₄)2 / ethyl acetate; diethyl ether / 0.5 h / 0 °C

With zinc(II) tetrahydroborate; potassium carbonate; In 1,4-dioxane; diethyl ether; water; ethyl acetate; acetone;

DOI:10.1039/P19920002971

Reference yield:

methyl 5-O-(E)-feruloyl-α-L-arabinofuranoside (134796-38-6) → (E)-3-{4-[2-Acetoxy-2-(4-acetoxy-3-methoxy-phenyl)-1-acetoxymethyl-ethoxy]-3-methoxy-phenyl}-acrylic acid (2S,3S,4R,5R)-3,4-diacetoxy-5-methoxy-tetrahydro-furan-2-ylmethyl ester (146252-15-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 78 percent / K₂CO₃ / acetone / 3 h / Heating

2: 82 percent / K₂CO₃ / dioxane; H₂O / 4 h

3: 94 percent / Zn(BH₄)2 / ethyl acetate; diethyl ether / 0.5 h / 0 °C

With zinc(II) tetrahydroborate; potassium carbonate; In 1,4-dioxane; diethyl ether; water; ethyl acetate; acetone;

DOI:10.1039/P19920002971

upstream raw materials:

acetic anhydride

methyl 5-O-<4-O-<2-(4-acetoxy-3-methoxyphenyl)-2-hydroxy-1-(hydroxymethyl)ethyl>feruloyl>-α-L-arabinofuranoside

4-acetoxy-β-bromo-3-methoxyacetophenone

methyl 5-O-(E)-feruloyl-α-L-arabinofuranoside

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