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

Base Information

Chemical Name:(2S,3S)-3-N-(tert-butyloxycarbonyl)amino-2-hydroxy-4-(4-benzyloxyphenyl)butanoic acid
CAS No.:145902-60-9
Molecular Formula:C₂₂H₂₇NO₆
Molecular Weight:401.459
Hs Code.:

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

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

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

There total 5 articles about (2S,3S)-3-N-(tert-butyloxycarbonyl)amino-2-hydroxy-4-(4-benzyloxyphenyl)butanoic acid 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: 99.0%

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

: 145902-60-9
(2S,3S)-3-N-(tert-butyloxycarbonyl)amino-2-hydroxy-4-(4-benzyloxyphenyl)butanoic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; methanol; for 3h;
DOI:10.1021/jm00054a004

Reference yield:

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

: 145902-60-9
(2S,3S)-3-N-(tert-butyloxycarbonyl)amino-2-hydroxy-4-(4-benzyloxyphenyl)butanoic acid

Guidance literature:: Multi-step reaction with 5 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

5: 99 percent / aq. LiOH / methanol; tetrahydrofuran / 3 h

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

Reference yield:

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

: 145902-60-9
(2S,3S)-3-N-(tert-butyloxycarbonyl)amino-2-hydroxy-4-(4-benzyloxyphenyl)butanoic acid

Guidance literature:: Multi-step reaction with 4 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

4: 99 percent / aq. LiOH / methanol; tetrahydrofuran / 3 h

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