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

Base Information

• Chemical Name: N^α-4-pentenoyl-phospho(1-(2-nitrophenyl)ethyl-2-tert-butyl)-L-threonine cyanomethyl ester
• CAS No.: 845619-11-6
• Molecular Formula: C₂₃H₃₂N₃O₉P
• Molecular Weight: 525.496

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

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

Chemical Property:

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

There total 4 articles about N^α-4-pentenoyl-phospho(1-(2-nitrophenyl)ethyl-2-tert-butyl)-L-threonine 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: 70.1%

Nα-4-pentenoyl-L-threonine cyanomethyl ester (845619-10-5) + 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-threonine cyanomethyl ester (845619-11-6)

Guidance literature:

N^α-4-pentenoyl-L-threonine 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-threonine cyanomethyl ester (845619-11-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 85.3 percent / N,N-diisopropylethylamine / tetrahydrofuran; H₂O

2.1: 71.7 percent / Diazabicyclo[5.4.0]undec-7-ene / 0 - 20 °C

3.1: 59 percent / trifluoroacetic acid; triisopropylsilane / 2 h / 0 °C

4.1: 4,5-dicyanoimidazole / tetrahydrofuran

4.2: 70.1 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-treonine (845619-08-1) → Nα-4-pentenoyl-phospho(1-(2-nitrophenyl)ethyl-2-tert-butyl)-L-threonine cyanomethyl ester (845619-11-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 71.7 percent / Diazabicyclo[5.4.0]undec-7-ene / 0 - 20 °C

2.1: 59 percent / trifluoroacetic acid; triisopropylsilane / 2 h / 0 °C

3.1: 4,5-dicyanoimidazole / tetrahydrofuran

3.2: 70.1 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-threonine 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-treonine

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