N^α-9-fluorenylmethoxycarbonyl-S-trityl-cysteine phenacyl ester

Base Information

• Chemical Name: N^α-9-fluorenylmethoxycarbonyl-S-trityl-cysteine phenacyl ester
• CAS No.: 233266-52-9
• Molecular Formula: C₄₅H₃₇NO₅S
• Molecular Weight: 703.858
• Mol file: 233266-52-9.mol

Synonyms:N^α-9-fluorenylmethoxycarbonyl-S-trityl-cysteine phenacyl ester

Chemical Property of N^α-9-fluorenylmethoxycarbonyl-S-trityl-cysteine phenacyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N^α-9-fluorenylmethoxycarbonyl-S-trityl-cysteine phenacyl ester

There total 1 articles about N^α-9-fluorenylmethoxycarbonyl-S-trityl-cysteine phenacyl 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: 97.0%

N-(9-fluorenylmethoxycarbonyl)-S-trityl-L-cysteine (103213-32-7,167015-11-4) + α-bromoacetophenone (70-11-1) → Nα-9-fluorenylmethoxycarbonyl-S-trityl-cysteine phenacyl ester (233266-52-9)

Guidance literature:

With triethylamine;

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

Reference yield: 84.0%

Nα-9-fluorenylmethoxycarbonyl-S-trityl-cysteine phenacyl ester (233266-52-9) → Nα-9-fluorenylmethoxycarbonyl-cysteine phenacyl ester (233266-53-0)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

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

Reference yield:

Nα-9-fluorenylmethoxycarbonyl-S-trityl-cysteine phenacyl ester (233266-52-9) → Fmoc-Cys-Phe-OMe

Guidance literature:

Multi-step reaction with 5 steps

1.1: 84 percent / TFA; triethylsilane / CH₂Cl₂ / 1 h / 20 °C

2.1: 70 percent / diisopropylethylamine / CH₂Cl₂ / 20 °C

3.1: 77 percent / zinc; acetic acid / 2 h / 20 °C

4.1: 63 percent / BOP; diisopropylethylamine

5.1: PhSiH₃ / Pd(PPh₃)4 / CH₂Cl₂ / 20 °C

5.2: 70 percent / mercaptoethanol; acetic acid / CH₂Cl₂ / 5 h

With triethylsilane; phenylsilane; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; acetic acid; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; 1.1: detritylation / 2.1: Condensation / 3.1: Reduction / 4.1: Condensation / 5.1: Decarboxylation / 5.2: dealkylation;

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

upstream raw materials:

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

α-bromoacetophenone

Downstream raw materials:

N^α-9-fluorenylmethoxycarbonyl-cysteine phenacyl ester

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

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

Fmoc-Cys(Fnam)-Phe-OMe

Refernces