trans-methyl 2-[2-(tert-butoxycarbonyl)-1-(3,4,5-trimethoxyphenyl)ethyl]-4,5-methylenedioxyphenylpropenoate

Base Information

• Chemical Name: trans-methyl 2-[2-(tert-butoxycarbonyl)-1-(3,4,5-trimethoxyphenyl)ethyl]-4,5-methylenedioxyphenylpropenoate
• CAS No.: 1428470-88-5
• Molecular Formula: C₂₇H₃₂O₉
• Molecular Weight: 500.546
• Mol file: 1428470-88-5.mol

Synonyms:trans-methyl 2-[2-(tert-butoxycarbonyl)-1-(3,4,5-trimethoxyphenyl)ethyl]-4,5-methylenedioxyphenylpropenoate

Chemical Property of trans-methyl 2-[2-(tert-butoxycarbonyl)-1-(3,4,5-trimethoxyphenyl)ethyl]-4,5-methylenedioxyphenylpropenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of trans-methyl 2-[2-(tert-butoxycarbonyl)-1-(3,4,5-trimethoxyphenyl)ethyl]-4,5-methylenedioxyphenylpropenoate

There total 5 articles about trans-methyl 2-[2-(tert-butoxycarbonyl)-1-(3,4,5-trimethoxyphenyl)ethyl]-4,5-methylenedioxyphenylpropenoate 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: 63.0%

(R)-tert-butyl 3-[4,5-methylenedioxy-2-(trifluoromethanesulfonyloxy)phenyl]-3-(3,4,5-trimethoxyphenyl)propanoate (1428470-87-4) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → trans-methyl 2-[2-(tert-butoxycarbonyl)-1-(3,4,5-trimethoxyphenyl)ethyl]-4,5-methylenedioxyphenylpropenoate (1428470-88-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 120 ℃; for 24h;

DOI:10.1021/jo400147f

Reference yield:

(2S,3R)-tert-butyl 2-benzylamino-3-(2-hydroxy-4,5-methylenedioxyphenyl)-3-(3,4,5-trimethoxyphenyl)propanoate (1428471-06-0) → trans-methyl 2-[2-(tert-butoxycarbonyl)-1-(3,4,5-trimethoxyphenyl)ethyl]-4,5-methylenedioxyphenylpropenoate (1428470-88-5)

Guidance literature:

Multi-step reaction with 3 steps

1: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran; water / 1 h / 20 °C

2: pyridine / dichloromethane / -40 - 0 °C

3: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate / N,N-dimethyl-formamide / 24 h / 120 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; samarium diiodide; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo400147f

Reference yield:

Sesamol (533-31-3) → trans-methyl 2-[2-(tert-butoxycarbonyl)-1-(3,4,5-trimethoxyphenyl)ethyl]-4,5-methylenedioxyphenylpropenoate (1428470-88-5)

Guidance literature:

Multi-step reaction with 4 steps

1: zinc trifluoromethanesulfonate / dichloromethane / 9 h / 30 °C

2: samarium diiodide; N,N,N,N,N,N-hexamethylphosphoric triamide / tetrahydrofuran; water / 1 h / 20 °C

3: pyridine / dichloromethane / -40 - 0 °C

4: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium hydrogencarbonate / N,N-dimethyl-formamide / 24 h / 120 °C

With pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; samarium diiodide; zinc trifluoromethanesulfonate; sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo400147f

upstream raw materials:

Sesamol

(2S,3R)-tert-butyl 2-benzylamino-3-(2-hydroxy-4,5-methylenedioxyphenyl)-3-(3,4,5-trimethoxyphenyl)propanoate

(R)-tert-butyl 3-(2-hydroxy-4,5-methylenedioxyphenyl)-3-(3,4,5-trimethoxyphenyl)propanoate

(R)-tert-butyl 3-[4,5-methylenedioxy-2-(trifluoromethanesulfonyloxy)phenyl]-3-(3,4,5-trimethoxyphenyl)propanoate