methyl (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-fluoro-6-phenyl-(E)-2-hexenoate

Base Information

• Chemical Name: methyl (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-fluoro-6-phenyl-(E)-2-hexenoate
• CAS No.: 144075-70-7
• Molecular Formula: C₁₈H₂₄FNO₄
• Molecular Weight: 337.391
• Mol file: 144075-70-7.mol

Synonyms:methyl (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-fluoro-6-phenyl-(E)-2-hexenoate

Chemical Property of methyl (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-fluoro-6-phenyl-(E)-2-hexenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-fluoro-6-phenyl-(E)-2-hexenoate

There total 12 articles about methyl (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-fluoro-6-phenyl-(E)-2-hexenoate 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: 83.0%

methyl (2S,3S)-3-benzyl-1-tert-butoxycarbonyl-2-[2-methoxycarbonyl-(E)-ethenyl]-aziridine (256463-36-2) → methyl (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-fluoro-6-phenyl-(E)-2-hexenoate (144075-70-7)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/S0040-4020(99)00865-0

Reference yield: 40.0%

methyl (4S,5S,2E)-5-amino-N-<(tert-butyloxy)carbonyl>-4-hydroxy-6-phenyl-2-hexanoate (134210-24-5) → methyl (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-fluoro-6-phenyl-(E)-2-hexenoate (144075-70-7) + methyl (2R,3S)-3-benzyl-1-tert-butoxycarbonyl-2-(2-methoxycarbonyl-(E)-ethenyl)-aziridine (144075-71-8)

Guidance literature:

With diethylamino-sulfur trifluoride; In dichloromethane; for 12h;

DOI:10.1016/S0040-4039(00)60117-X

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → methyl (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-fluoro-6-phenyl-(E)-2-hexenoate (144075-70-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / Et₃N; 2-chloro-1-methylpyridinium iodide / CH₂Cl₂ / Heating

2: 96 percent / tetrahydrofuran / -40 °C

3: 70 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 66 h / 20 °C

4: MnO₂ / hexane; CH₂Cl₂ / 0.5 h / 0 °C

5: pyridinium dichromate / dimethylformamide / 18 h / 20 °C

6: NaBH₄; CeCl₃*7H₂O / tetrahydrofuran; methanol / 0.17 h / 20 °C

7: 91 percent / diethyl azodicarboxylate; Ph₃P / tetrahydrofuran / 0.5 h / Heating

8: 83 percent / diethylaminosulfur trifluoride / CH₂Cl₂ / 12 h / 20 °C

With manganese(IV) oxide; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; diethylamino-sulfur trifluoride; 2-chloro-1-methyl-pyridinium iodide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Grignard reaction / 3: Oxidation / 4: Oxidation / 5: Oxidation / 6: Reduction / 7: Cyclization / 8: Fluorination;

DOI:10.1016/S0040-4020(99)00865-0

upstream raw materials:

methyl (4S,5S,2E)-5-amino-N-<(tert-butyloxy)carbonyl>-4-hydroxy-6-phenyl-2-hexanoate

methyl (2S,3S)-3-benzyl-1-tert-butoxycarbonyl-2-[2-methoxycarbonyl-(E)-ethenyl]-aziridine

N-tert-butoxycarbonyl-L-phenylalanine

Boc-Phe-OH N,O-dimethyl hydroxamate