4-ethyl 3-methyl rel-(3R,4S,5S)-2-oxo-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-3,4-dicarboxylate

Base Information

• Chemical Name: 4-ethyl 3-methyl rel-(3R,4S,5S)-2-oxo-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-3,4-dicarboxylate
• CAS No.: 134302-93-5
• Molecular Formula: C₁₈H₂₂O₉
• Molecular Weight: 382.367
• Mol file: 134302-93-5.mol

Synonyms:4-ethyl 3-methyl rel-(3R,4S,5S)-2-oxo-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-3,4-dicarboxylate

Chemical Property of 4-ethyl 3-methyl rel-(3R,4S,5S)-2-oxo-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-3,4-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-ethyl 3-methyl rel-(3R,4S,5S)-2-oxo-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-3,4-dicarboxylate

There total 1 articles about 4-ethyl 3-methyl rel-(3R,4S,5S)-2-oxo-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-3,4-dicarboxylate 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: 55.0%

ethyl (E)-3-(3,4,5-trimethoxyphenyl)acrylate (1878-29-1,30273-65-5,31892-98-5) + monomethyl monopotassium malonate (38330-80-2) → (2R,3R)-5-Oxo-2-(3,4,5-trimethoxy-phenyl)-tetrahydro-furan-3-carboxylic acid ethyl ester + 4-ethyl 3-methyl rel-(3R,4S,5S)-2-oxo-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-3,4-dicarboxylate (134302-93-5)

Guidance literature:

With manganese triacetate; In acetic acid; at 70 ℃; for 0.416667h;

DOI:10.1055/s-1991-26444

Reference yield:

4-ethyl 3-methyl rel-(3R,4S,5S)-2-oxo-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-3,4-dicarboxylate (134302-93-5) → 3-ethyl 2-methyl rel-(2R,3S,4R)-6,7-methylenedioxy-1-oxo-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate (134302-94-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) KH / 1.) THF, 24 deg C, 1 h, 2.) THF, 24 deg C, 23 h

2: 91 percent / SnCl₄ / CHCl₃ / 12 h / 24 °C

With tin(IV) chloride; potassium hydride; In chloroform;

DOI:10.1055/s-1991-26444

Reference yield:

4-ethyl 3-methyl rel-(3R,4S,5S)-2-oxo-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-3,4-dicarboxylate (134302-93-5) → ethyl rel-(3R,4R)-6,7-methylenedioxy-1-oxo-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-3-carboxylate (75404-00-1,81649-61-8,106044-39-7,112026-11-6,114947-14-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) KH / 1.) THF, 24 deg C, 1 h, 2.) THF, 24 deg C, 23 h

2: 91 percent / SnCl₄ / CHCl₃ / 12 h / 24 °C

3: 100 percent / KOAc, AcOH / 14 h / Heating

With potassium acetate; tin(IV) chloride; potassium hydride; acetic acid; In chloroform;

DOI:10.1055/s-1991-26444

upstream raw materials:

ethyl (E)-3-(3,4,5-trimethoxyphenyl)acrylate

monomethyl monopotassium malonate

Downstream raw materials:

4-ethyl 3-methyl rel-(3R,4S,5S)-2-oxo-3-piperonyloyl-5-(3,4,5-trimethoxyphenyl)tetrahydrofuran-3,4-dicarboxylate

3-ethyl 2-methyl rel-(2R,3S,4R)-6,7-methylenedioxy-1-oxo-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-2,3-dicarboxylate

ethyl rel-(3R,4R)-6,7-methylenedioxy-1-oxo-4-(3,4,5-trimethoxyphenyl)-1,2,3,4-tetrahydronaphthalene-3-carboxylate