N^α-4-pentenoyl-phospho(1-(2-nitrophenyl)ethyl-2-tert-butyl)-L-serine cyanomethyl ester

Base Information

• Chemical Name: N^α-4-pentenoyl-phospho(1-(2-nitrophenyl)ethyl-2-tert-butyl)-L-serine cyanomethyl ester
• CAS No.: 845619-06-9
• Molecular Formula: C₂₂H₃₀N₃O₉P
• Molecular Weight: 511.469

Synonyms:N^α-4-pentenoyl-phospho(1-(2-nitrophenyl)ethyl-2-tert-butyl)-L-serine cyanomethyl ester

Chemical Property of N^α-4-pentenoyl-phospho(1-(2-nitrophenyl)ethyl-2-tert-butyl)-L-serine cyanomethyl ester

Chemical Property:

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Technology Process of N^α-4-pentenoyl-phospho(1-(2-nitrophenyl)ethyl-2-tert-butyl)-L-serine cyanomethyl ester

There total 4 articles about N^α-4-pentenoyl-phospho(1-(2-nitrophenyl)ethyl-2-tert-butyl)-L-serine cyanomethyl 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: 68.2%

Nα-4-pentenoyl-L-serine cyanomethyl ester (845619-05-8) + O-1-(2-nitrophenyl)ethyl-O'-tert-butyl-N,N-diethyl phosphoramidite (845619-02-5) → Nα-4-pentenoyl-phospho(1-(2-nitrophenyl)ethyl-2-tert-butyl)-L-serine cyanomethyl ester (845619-06-9)

Guidance literature:

N^α-4-pentenoyl-L-serine cyanomethyl ester; O-1-(2-nitrophenyl)ethyl-O'-tert-butyl-N,N-diethyl phosphoramidite; With 4,5-dicyano-1H-imidazole; In tetrahydrofuran;

With tert.-butylhydroperoxide; In decane; dichloromethane; for 1h;

DOI:10.1021/ja043875c

Reference yield:

4-pentenoic anhydride (63521-92-6) → Nα-4-pentenoyl-phospho(1-(2-nitrophenyl)ethyl-2-tert-butyl)-L-serine cyanomethyl ester (845619-06-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 93.7 percent / N,N-diisopropylethylamine / tetrahydrofuran; H₂O

2.1: 79.9 percent / Diazabicyclo[5.4.0]undec-7-ene / 0 - 20 °C

3.1: 25.6 percent / trifluoroacetic acid; triisopropylsilane / 4 h / 0 °C

4.1: 4,5-dicyanoimidazole / tetrahydrofuran

4.2: 68.2 percent / tert-butyl hydroperoxide / CH₂Cl₂; decane / 1 h

With 4,5-dicyano-1H-imidazole; 1,2-diazabicyclo[5.4.0]undec-7-ene; chlorotriisopropylsilane; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; water;

DOI:10.1021/ja043875c

Reference yield:

Nα-4-pentenoyl-O-tert-butyl-L-serine (845619-03-6) → Nα-4-pentenoyl-phospho(1-(2-nitrophenyl)ethyl-2-tert-butyl)-L-serine cyanomethyl ester (845619-06-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 79.9 percent / Diazabicyclo[5.4.0]undec-7-ene / 0 - 20 °C

2.1: 25.6 percent / trifluoroacetic acid; triisopropylsilane / 4 h / 0 °C

3.1: 4,5-dicyanoimidazole / tetrahydrofuran

3.2: 68.2 percent / tert-butyl hydroperoxide / CH₂Cl₂; decane / 1 h

With 4,5-dicyano-1H-imidazole; 1,2-diazabicyclo[5.4.0]undec-7-ene; chlorotriisopropylsilane; trifluoroacetic acid; In tetrahydrofuran;

DOI:10.1021/ja043875c

upstream raw materials:

N^α-4-pentenoyl-L-serine cyanomethyl ester

O-1-(2-nitrophenyl)ethyl-O'-tert-butyl-N,N-diethyl phosphoramidite

4-pentenoic anhydride

N^α-4-pentenoyl-O-tert-butyl-L-serine

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