(E)-3-(3-Pentafluorophenylmethoxy-phenyl)-but-2-enoic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[(E)-3-(3-pentafluorophenylmethoxy-phenyl)-but-2-enoyloxymethyl]-tetrahydro-furan-3-yl ester

Base Information

• Chemical Name: (E)-3-(3-Pentafluorophenylmethoxy-phenyl)-but-2-enoic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[(E)-3-(3-pentafluorophenylmethoxy-phenyl)-but-2-enoyloxymethyl]-tetrahydro-furan-3-yl ester
• CAS No.: 131702-06-2
• Molecular Formula: C₄₄H₃₂F₁₀N₂O₉
• Molecular Weight: 922.73

Synonyms:(E)-3-(3-Pentafluorophenylmethoxy-phenyl)-but-2-enoic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[(E)-3-(3-pentafluorophenylmethoxy-phenyl)-but-2-enoyloxymethyl]-tetrahydro-furan-3-yl ester

Chemical Property of (E)-3-(3-Pentafluorophenylmethoxy-phenyl)-but-2-enoic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[(E)-3-(3-pentafluorophenylmethoxy-phenyl)-but-2-enoyloxymethyl]-tetrahydro-furan-3-yl ester

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Technology Process of (E)-3-(3-Pentafluorophenylmethoxy-phenyl)-but-2-enoic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[(E)-3-(3-pentafluorophenylmethoxy-phenyl)-but-2-enoyloxymethyl]-tetrahydro-furan-3-yl ester

There total 6 articles about (E)-3-(3-Pentafluorophenylmethoxy-phenyl)-but-2-enoic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[(E)-3-(3-pentafluorophenylmethoxy-phenyl)-but-2-enoyloxymethyl]-tetrahydro-furan-3-yl 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:

3-Hydroxyacetophenone (121-71-1) → (E)-3-(3-Pentafluorophenylmethoxy-phenyl)-but-2-enoic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[(E)-3-(3-pentafluorophenylmethoxy-phenyl)-but-2-enoyloxymethyl]-tetrahydro-furan-3-yl ester (131702-06-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 92 percent / aq.NaOH, tetra-n-butylammonium sulfate / CH₂Cl₂ / 3 h / Ambient temperature; similar yield with K₂CO₃ in acetone (reflux, 2 h)

2: 27 percent / xylene / 34 h / Heating

3: hydrolysis

4: 98 percent / SOCl₂ / benzene / 20 h / 90 °C

With sodium hydroxide; thionyl chloride; tetrabutylammonium sulfate; In dichloromethane; xylene; benzene;

DOI:10.1016/S0040-4020(01)87912-6

Reference yield:

m-(pentafluorobenzyloxy)acetophenone (131693-26-0) → (E)-3-(3-Pentafluorophenylmethoxy-phenyl)-but-2-enoic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[(E)-3-(3-pentafluorophenylmethoxy-phenyl)-but-2-enoyloxymethyl]-tetrahydro-furan-3-yl ester (131702-06-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 27 percent / xylene / 34 h / Heating

2: hydrolysis

3: 98 percent / SOCl₂ / benzene / 20 h / 90 °C

With thionyl chloride; In xylene; benzene;

DOI:10.1016/S0040-4020(01)87912-6

Reference yield:

m-pentafluorobenzyloxy-β-methyl-cinnamic acid (131693-36-2) → (E)-3-(3-Pentafluorophenylmethoxy-phenyl)-but-2-enoic acid (2R,3S,5R)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-2-[(E)-3-(3-pentafluorophenylmethoxy-phenyl)-but-2-enoyloxymethyl]-tetrahydro-furan-3-yl ester (131702-06-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / SOCl₂ / benzene / 20 h / 90 °C

With thionyl chloride; In benzene;

DOI:10.1016/S0040-4020(01)87912-6

upstream raw materials:

m-(pentafluorobenzyloxy)-E-3-methylcinnamoyl chloride

thymidine

3-Hydroxyacetophenone

m-(pentafluorobenzyloxy)acetophenone

Downstream raw materials:

3',5'-bis-O-<(m-pentafluorobenzyloxy)-E-3-methylcinnamoyl>-N3-methylthymidine

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