(3S)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-(2',3',5',6'-tetrafluorophenoxy)-4-oxopentanoic acid tert-butyl ester

Base Information

Chemical Name:(3S)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-(2',3',5',6'-tetrafluorophenoxy)-4-oxopentanoic acid tert-butyl ester
CAS No.:254750-76-0
Molecular Formula:C₂₈H₃₂F₄N₂O₇
Molecular Weight:584.565
Hs Code.:

Synonyms:(3S)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-(2',3',5',6'-tetrafluorophenoxy)-4-oxopentanoic acid tert-butyl ester

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Chemical Property of (3S)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-(2',3',5',6'-tetrafluorophenoxy)-4-oxopentanoic acid tert-butyl ester

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Technology Process of (3S)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-(2',3',5',6'-tetrafluorophenoxy)-4-oxopentanoic acid tert-butyl ester

There total 4 articles about (3S)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-(2',3',5',6'-tetrafluorophenoxy)-4-oxopentanoic 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: 79.0%

: 769-39-1,85303-67-9
2,3,5,6-tetraflourophenol

: 168319-04-8
(3S)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-bromo-4-oxopentanoic acid tert-butyl ester

: 254750-76-0
(3S)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-(2',3',5',6'-tetrafluorophenoxy)-4-oxopentanoic acid tert-butyl ester

Guidance literature:: With potassium fluoride; In tetrahydrofuran;

Reference yield:

: 168319-04-8
(3S)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-bromo-4-oxopentanoic acid tert-butyl ester

: 2,3,5,6-tetrafluorophenol potassium salt

: 254750-76-0
(3S)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-(2',3',5',6'-tetrafluorophenoxy)-4-oxopentanoic acid tert-butyl ester

Guidance literature:: With sodium iodide; In acetone; at 20 ℃;
DOI:10.1016/j.bmcl.2003.12.106

Reference yield:

: Z-Val-Asp(O-tBu)-OH

: 254750-76-0
(3S)-3-[(N-benzyloxycarbonyl)valinyl]amino-5-(2',3',5',6'-tetrafluorophenoxy)-4-oxopentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: ClCO₂iBu; NMM / tetrahydrofuran / 0.5 h / -10 °C

1.2: diethyl ether / 1 h / 0 °C

2.1: aq. HBr / tetrahydrofuran / 0.25 h / 0 - 20 °C

3.1: NaI / acetone / 20 °C

With 4-methyl-morpholine; hydrogen bromide; sodium iodide; isobutyl chloroformate; In tetrahydrofuran; acetone;
DOI:10.1016/j.bmcl.2003.12.106