(2S,3S)-3-N-(tert-butyloxycarbonyl)amino-2-hydroxy-4-(4-benzyloxyphenyl)butanoic acid methyl ester

Base Information

Chemical Name:(2S,3S)-3-N-(tert-butyloxycarbonyl)amino-2-hydroxy-4-(4-benzyloxyphenyl)butanoic acid methyl ester
CAS No.:145902-57-4
Molecular Formula:C₂₃H₂₉NO₆
Molecular Weight:415.486
Hs Code.:

Synonyms:(2S,3S)-3-N-(tert-butyloxycarbonyl)amino-2-hydroxy-4-(4-benzyloxyphenyl)butanoic acid methyl ester

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Chemical Property of (2S,3S)-3-N-(tert-butyloxycarbonyl)amino-2-hydroxy-4-(4-benzyloxyphenyl)butanoic acid methyl ester

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Technology Process of (2S,3S)-3-N-(tert-butyloxycarbonyl)amino-2-hydroxy-4-(4-benzyloxyphenyl)butanoic acid methyl ester

There total 4 articles about (2S,3S)-3-N-(tert-butyloxycarbonyl)amino-2-hydroxy-4-(4-benzyloxyphenyl)butanoic acid methyl 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: 44.0%

: 100-39-0
benzyl bromide

: (S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-(4-hydroxy-phenyl)-butyric acid methyl ester

: 145902-57-4
(2S,3S)-3-N-(tert-butyloxycarbonyl)amino-2-hydroxy-4-(4-benzyloxyphenyl)butanoic acid methyl ester

: 145902-58-5
(2R,3S)-3-N-(tert-butyloxycarbonyl)amino-2-hydroxy-4-(4-benzyloxyphenyl)butanoic acid methyl ester

Guidance literature:: With tetra-(n-butyl)ammonium iodide; caesium carbonate; In N,N-dimethyl-formamide; for 5h;
DOI:10.1021/jm00054a004

Reference yield:

: 27513-44-6
N-tert-butoxycarbonyl-O-benzyl-(S)-tyrosine methyl ester

: 145902-57-4
(2S,3S)-3-N-(tert-butyloxycarbonyl)amino-2-hydroxy-4-(4-benzyloxyphenyl)butanoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: diisobutylaluminium hydride / toluene; hexane / -77 °C

2: sodium metabisulfite / H₂O / 5 h / Ambient temperature

3: 1.) 25percent aq. HCl, 2.) Na₂CO₃, di-tert-butyl dicarbonate, 3.) KHCO₃

4: 29 percent / Cs₂CO₃, (n-Bu)4NI / dimethylformamide / 5 h

With hydrogenchloride; sodium disulfite; di-tert-butyl dicarbonate; tetra-(n-butyl)ammonium iodide; diisobutylaluminium hydride; sodium carbonate; potassium hydrogencarbonate; caesium carbonate; In hexane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jm00054a004

Reference yield:

: 82689-15-4
O-benzyl-N-(tert-butoxycarbonyl)-L-tyrosinal

: 145902-57-4
(2S,3S)-3-N-(tert-butyloxycarbonyl)amino-2-hydroxy-4-(4-benzyloxyphenyl)butanoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: sodium metabisulfite / H₂O / 5 h / Ambient temperature

2: 1.) 25percent aq. HCl, 2.) Na₂CO₃, di-tert-butyl dicarbonate, 3.) KHCO₃

3: 29 percent / Cs₂CO₃, (n-Bu)4NI / dimethylformamide / 5 h

With hydrogenchloride; sodium disulfite; di-tert-butyl dicarbonate; tetra-(n-butyl)ammonium iodide; sodium carbonate; potassium hydrogencarbonate; caesium carbonate; In water; N,N-dimethyl-formamide;
DOI:10.1021/jm00054a004