N^α-9-fluorenylmethoxycarbonyl-S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(allyloxycarbonyl)aminomethyl]cysteine

Base Information

• Chemical Name: N^α-9-fluorenylmethoxycarbonyl-S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(allyloxycarbonyl)aminomethyl]cysteine
• CAS No.: 233266-63-2
• Molecular Formula: C₃₄H₃₃F₄N₃O₆S
• Molecular Weight: 687.712

Synonyms:N^α-9-fluorenylmethoxycarbonyl-S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(allyloxycarbonyl)aminomethyl]cysteine

Chemical Property of N^α-9-fluorenylmethoxycarbonyl-S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(allyloxycarbonyl)aminomethyl]cysteine

Chemical Property:

Purity/Quality:

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MSDS Files:

Useful:

Technology Process of N^α-9-fluorenylmethoxycarbonyl-S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(allyloxycarbonyl)aminomethyl]cysteine

There total 10 articles about N^α-9-fluorenylmethoxycarbonyl-S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(allyloxycarbonyl)aminomethyl]cysteine 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: 77.0%

Nα-9-fluorenylmethoxycarbonyl-S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(allyloxycarbonyl)aminomethyl]cysteine phenacyl ester (233266-62-1) → Nα-9-fluorenylmethoxycarbonyl-S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(allyloxycarbonyl)aminomethyl]cysteine (233266-63-2)

Guidance literature:

With acetic acid; zinc; at 20 ℃; for 2h;

DOI:10.1016/S0040-4020(99)00323-3

Reference yield:

piperidine (110-89-4) → Nα-9-fluorenylmethoxycarbonyl-S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(allyloxycarbonyl)aminomethyl]cysteine (233266-63-2)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 93 percent / dimethylformamide / 72 h / 20 °C

2.1: sodium hydride / dimethylformamide

2.2: 83 percent / dimethylformamide / 2 h / 20 °C

3.1: 71 percent / CH₂Cl₂ / 8 h / 20 °C

4.1: 70 percent / diisopropylethylamine / CH₂Cl₂ / 20 °C

5.1: 77 percent / zinc; acetic acid / 2 h / 20 °C

With sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; zinc; In dichloromethane; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Metallation / 2.2: Alkylation / 3.1: Alkylation / 4.1: Condensation / 5.1: Reduction;

DOI:10.1016/S0040-4020(99)00323-3

Reference yield:

2,3,4,5,6-pentafluoroaniline (771-60-8) → Nα-9-fluorenylmethoxycarbonyl-S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(allyloxycarbonyl)aminomethyl]cysteine (233266-63-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: ethylmagnesium chloride / tetrahydrofuran / 1 h / 20 °C

1.2: 96 percent / tetrahydrofuran / 24 h / 50 °C

2.1: 93 percent / dimethylformamide / 72 h / 20 °C

3.1: sodium hydride / dimethylformamide

3.2: 83 percent / dimethylformamide / 2 h / 20 °C

4.1: 71 percent / CH₂Cl₂ / 8 h / 20 °C

5.1: 70 percent / diisopropylethylamine / CH₂Cl₂ / 20 °C

6.1: 77 percent / zinc; acetic acid / 2 h / 20 °C

With ethylmagnesium chloride; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Acylation / 2.1: Substitution / 3.1: Metallation / 3.2: Alkylation / 4.1: Alkylation / 5.1: Condensation / 6.1: Reduction;

DOI:10.1016/S0040-4020(99)00323-3

upstream raw materials:

N^α-9-fluorenylmethoxycarbonyl-S-[N-[2,3,5,6-tetrafluoro-4-(N'-piperidino)phenyl]-N-(allyloxycarbonyl)aminomethyl]cysteine phenacyl ester

piperidine

2,3,4,5,6-pentafluoroaniline

N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine

Downstream raw materials:

Fmoc-Cys(Fnam)-Phe-OMe

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