L-Proline, 1-[(2S)-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-4-penten-1-yl]- 5-(dimethylphenylsilyl)-, methyl ester

Base Information

• Chemical Name: L-Proline, 1-[(2S)-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-4-penten-1-yl]- 5-(dimethylphenylsilyl)-, methyl ester
• CAS No.: 916049-29-1
• Molecular Formula: C27H30N2O5Si
• Molecular Weight: 490.631
• Mol file: 916049-29-1.mol

Synonyms:

Chemical Property of L-Proline, 1-[(2S)-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-4-penten-1-yl]- 5-(dimethylphenylsilyl)-, methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of L-Proline, 1-[(2S)-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-4-penten-1-yl]- 5-(dimethylphenylsilyl)-, methyl ester

There total 6 articles about L-Proline, 1-[(2S)-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxo-4-penten-1-yl]- 5-(dimethylphenylsilyl)-, methyl 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:

5-(dimethylphenylsilyl)pyrrolidine-1,2-dicarboxylic acid 1-benzyl 2-methyl ester (916049-26-8) → 5-(dimethylphenylsilyl)-1-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pent-4-enoyl]pyrrolidine-2-carboxylic acid methyl ester (916049-29-1)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen / palladium hydroxide / methanol / 12 h / 20 °C

2: 381 mg / triethylamine / diethyl ether / 12 h / 20 °C

With hydrogen; triethylamine; palladium dihydroxide; In methanol; diethyl ether;

DOI:10.1021/ja064737l

Reference yield:

(5S)-2-Methoxy-1-[(benzyloxy)carbonyl]-5-methoxycarbonylpyrrolidine (214072-10-3) → 5-(dimethylphenylsilyl)-1-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pent-4-enoyl]pyrrolidine-2-carboxylic acid methyl ester (916049-29-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 85 percent / magnesium sulfate; trifluoroacetic acid / CH₂Cl₂ / 2 h / 20 °C

2.1: lithium / tetrahydrofuran / 12 h / 20 °C

2.2: copper cyanide / tetrahydrofuran; diethyl ether / 0.17 h / 20 °C

2.3: 71 percent / tetrahydrofuran; diethyl ether / 1.5 h / -78 °C

3.1: hydrogen / palladium hydroxide / methanol / 12 h / 20 °C

4.1: 381 mg / triethylamine / diethyl ether / 12 h / 20 °C

With hydrogen; lithium; magnesium sulfate; triethylamine; trifluoroacetic acid; palladium dihydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/ja064737l

Reference yield:

5-(dimethyl-phenyl-silanyl)-pyrrolidine-2-carboxylic acid methyl ester + 2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pent-4-enoic acid chloride (916049-18-8) → 5-(dimethylphenylsilyl)-1-[2-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pent-4-enoyl]pyrrolidine-2-carboxylic acid methyl ester (916049-29-1)

Guidance literature:

With triethylamine; In diethyl ether; at 20 ℃; for 12h;

DOI:10.1021/ja064737l

upstream raw materials:

2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-pent-4-enoic acid chloride

5-(dimethylphenylsilyl)pyrrolidine-1,2-dicarboxylic acid 1-benzyl 2-methyl ester

L-allylglycine

N-ethoxycarbonylphthalimide