(2S,3S)-4-(4-Benzyloxy-phenyl)-3-tert-butoxycarbonylamino-2-hydroxy-butyric acid benzyl ester

Base Information

Chemical Name:(2S,3S)-4-(4-Benzyloxy-phenyl)-3-tert-butoxycarbonylamino-2-hydroxy-butyric acid benzyl ester
CAS No.:145902-61-0
Molecular Formula:C₂₉H₃₃NO₆
Molecular Weight:491.584
Hs Code.:

Synonyms:(2S,3S)-4-(4-Benzyloxy-phenyl)-3-tert-butoxycarbonylamino-2-hydroxy-butyric acid benzyl ester

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Chemical Property of (2S,3S)-4-(4-Benzyloxy-phenyl)-3-tert-butoxycarbonylamino-2-hydroxy-butyric acid benzyl ester

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Technology Process of (2S,3S)-4-(4-Benzyloxy-phenyl)-3-tert-butoxycarbonylamino-2-hydroxy-butyric acid benzyl ester

There total 6 articles about (2S,3S)-4-(4-Benzyloxy-phenyl)-3-tert-butoxycarbonylamino-2-hydroxy-butyric acid benzyl 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: 81.0%

: 100-39-0
benzyl bromide

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

: 145902-61-0
(2S,3S)-4-(4-Benzyloxy-phenyl)-3-tert-butoxycarbonylamino-2-hydroxy-butyric acid benzyl 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

: 145902-61-0
(2S,3S)-4-(4-Benzyloxy-phenyl)-3-tert-butoxycarbonylamino-2-hydroxy-butyric acid benzyl ester

Guidance literature:: Multi-step reaction with 6 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

6: 81 percent / Cs₂CO₃, (n-Bu)4NI / dimethylformamide / 5 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

: 145902-61-0
(2S,3S)-4-(4-Benzyloxy-phenyl)-3-tert-butoxycarbonylamino-2-hydroxy-butyric acid benzyl ester

Guidance literature:: Multi-step reaction with 5 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

5: 81 percent / Cs₂CO₃, (n-Bu)4NI / dimethylformamide / 5 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