N-(1-benzyloxycarbonyl-2-phenyl-ethyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-succinamic acid tert-butyl ester

Base Information

• Chemical Name: N-(1-benzyloxycarbonyl-2-phenyl-ethyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-succinamic acid tert-butyl ester
• CAS No.: 200936-33-0
• Molecular Formula: C₃₉H₄₀N₂O₇
• Molecular Weight: 648.756

Synonyms:N-(1-benzyloxycarbonyl-2-phenyl-ethyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-succinamic acid tert-butyl ester

Chemical Property of N-(1-benzyloxycarbonyl-2-phenyl-ethyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-succinamic acid tert-butyl ester

Chemical Property:

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Technology Process of N-(1-benzyloxycarbonyl-2-phenyl-ethyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-succinamic acid tert-butyl ester

There total 1 articles about N-(1-benzyloxycarbonyl-2-phenyl-ethyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-succinamic acid tert-butyl 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: 89.5%

L-phenylalanine benzyl ester p-toluene-sulfonic acid salt (1738-78-9) + FMOC-Asp(O-t-Bu)-F (130859-01-7) → N-(1-benzyloxycarbonyl-2-phenyl-ethyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-succinamic acid tert-butyl ester (200936-33-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1016/S0040-4020(99)00344-0

Reference yield: 73.7%

N-(1-benzyloxycarbonyl-2-phenyl-ethyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-succinamic acid tert-butyl ester (200936-33-0) → Fmoc-L-Asp(O-t-Bu)-L-Phe-OH (87867-02-5)

Guidance literature:

With ammonium formate; palladium on activated charcoal; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 0.75h;

DOI:10.1016/S0040-4020(99)00344-0

Reference yield:

N-(1-benzyloxycarbonyl-2-phenyl-ethyl)-3-(9H-fluoren-9-ylmethoxycarbonylamino)-succinamic acid tert-butyl ester (200936-33-0) → Fmoc-L-Asp-D-Phe-L-Lys-NH2

Guidance literature:

Multi-step reaction with 2 steps

1.1: 73.7 percent / ammonium formate / Pd-C / methanol; tetrahydrofuran / 0.75 h / 0 - 20 °C

2.1: piperidine / dimethylformamide / 0.12 h

2.2: HATU; diisopropylethylamine / dimethylformamide / 13 h

2.3: trifluoroacetic acid; water / 1.5 h / 20 °C

With piperidine; ammonium formate; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1.1: Hydrogenolysis / 2.1: Solid phase reaction / 2.2: Solid phase reaction / 2.3: Solid phase reaction;

DOI:10.1016/S0040-4020(99)00344-0

upstream raw materials:

L-phenylalanine benzyl ester p-toluene-sulfonic acid salt

FMOC-Asp(O-t-Bu)-F

Downstream raw materials:

Fmoc-L-Asp(O-t-Bu)-L-Phe-OH

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