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

Base Information

Chemical Name:(4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-(E)-2-hexenoate
CAS No.:134210-25-6
Molecular Formula:C₁₈H₂₅NO₅
Molecular Weight:335.4
Hs Code.:

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

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

Chemical Property:

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

There total 8 articles about (4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-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:

: 178259-04-6
methyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-4-oxo-6-phenyl-(E)-2-hexenoate

: 134210-25-6
(4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-(E)-2-hexenoate

: 134210-24-5
methyl (4S,5S,2E)-5-amino-N-<(tert-butyloxy)carbonyl>-4-hydroxy-6-phenyl-2-hexanoate

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride; In tetrahydrofuran; methanol; at 20 ℃; for 0.166667h;
DOI:10.1016/S0040-4020(99)00865-0

Reference yield:

: 13734-34-4
N-tert-butoxycarbonyl-L-phenylalanine

: 134210-25-6
(4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-(E)-2-hexenoate

Guidance literature:: Multi-step reaction with 6 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

With manganese(IV) oxide; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; 2-chloro-1-methyl-pyridinium iodide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1: Substitution / 2: Grignard reaction / 3: Oxidation / 4: Oxidation / 5: Oxidation / 6: Reduction;
DOI:10.1016/S0040-4020(99)00865-0

Reference yield:

: 87694-53-9
Boc-Phe-OH N,O-dimethyl hydroxamate

: 134210-25-6
(4R,5S)-5-[(tert-butoxycarbonyl)amino]-4-hydroxy-6-phenyl-(E)-2-hexenoate

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / tetrahydrofuran / -40 °C

2: 70 percent / 3-chloroperbenzoic acid / CH₂Cl₂ / 66 h / 20 °C

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

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

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

With manganese(IV) oxide; sodium tetrahydroborate; dipyridinium dichromate; cerium(III) chloride; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; 1: Grignard reaction / 2: Oxidation / 3: Oxidation / 4: Oxidation / 5: Reduction;
DOI:10.1016/S0040-4020(99)00865-0