(2S,3S)-2-tert-Butoxycarbonylamino-3-hydroxy-3-(4-hydroxy-phenyl)-propionic acid

Base Information

Chemical Name:(2S,3S)-2-tert-Butoxycarbonylamino-3-hydroxy-3-(4-hydroxy-phenyl)-propionic acid
CAS No.:607358-36-1
Molecular Formula:C₁₄H₁₉NO₆
Molecular Weight:297.308
Hs Code.:

Synonyms:(2S,3S)-2-tert-Butoxycarbonylamino-3-hydroxy-3-(4-hydroxy-phenyl)-propionic acid

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Chemical Property of (2S,3S)-2-tert-Butoxycarbonylamino-3-hydroxy-3-(4-hydroxy-phenyl)-propionic acid

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Technology Process of (2S,3S)-2-tert-Butoxycarbonylamino-3-hydroxy-3-(4-hydroxy-phenyl)-propionic acid

There total 3 articles about (2S,3S)-2-tert-Butoxycarbonylamino-3-hydroxy-3-(4-hydroxy-phenyl)-propionic 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: 49.0%

: 607358-20-3
3-(4-acetoxy-phenyl)-2-tert-butoxycarbonylamino-3-oxo-propionic acid ethyl ester

: 607358-36-1
(2S,3S)-2-tert-Butoxycarbonylamino-3-hydroxy-3-(4-hydroxy-phenyl)-propionic acid

: (2S,3S)-2-tert-Butoxycarbonylamino-3-hydroxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester

: 607358-38-3
(2R,3R)-2-tert-Butoxycarbonylamino-3-hydroxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester

Guidance literature:: 3-(4-acetoxy-phenyl)-2-tert-butoxycarbonylamino-3-oxo-propionic acid ethyl ester; With sodium tetrahydroborate; In ethanol; at -20 ℃; for 0.25h;

With Aspergillus melleus protease; In phosphate buffer; at 23 ℃; for 3h; pH=7; Enzymatic reaction;
DOI:10.1021/ol035101r

Reference yield:

: 137686-07-8,137401-45-7
2-{[(tert-butoxy)carbonyl]amino}-3-ethoxy-3-oxopropanoic acid

: 607358-36-1
(2S,3S)-2-tert-Butoxycarbonylamino-3-hydroxy-3-(4-hydroxy-phenyl)-propionic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: Et₃N; MgCl₂ / tetrahydrofuran / 2.5 h / cooling

1.2: tetrahydrofuran / 12 h / 20 °C

2.1: NaBH₄ / ethanol / 0.25 h / -20 °C

2.2: 49 percent / Aspergillus melleus protease / aq. phosphate buffer / 3 h / 23 °C / pH 7 / Enzymatic reaction

With sodium tetrahydroborate; triethylamine; magnesium chloride; In tetrahydrofuran; ethanol;
DOI:10.1021/ol035101r

Reference yield:

: 102831-44-7
diethyl tert-butoxycarbonylaminomalonate

: 607358-36-1
(2S,3S)-2-tert-Butoxycarbonylamino-3-hydroxy-3-(4-hydroxy-phenyl)-propionic acid

Guidance literature:: Multi-step reaction with 3 steps

1.1: 84 percent / pig liver esterase / aq. phosphate buffer / 2 h / 23 °C / pH 7.0 / Enzymatic reaction

2.1: Et₃N; MgCl₂ / tetrahydrofuran / 2.5 h / cooling

2.2: tetrahydrofuran / 12 h / 20 °C

3.1: NaBH₄ / ethanol / 0.25 h / -20 °C

3.2: 49 percent / Aspergillus melleus protease / aq. phosphate buffer / 3 h / 23 °C / pH 7 / Enzymatic reaction

With sodium tetrahydroborate; pig liver esterase; triethylamine; magnesium chloride; In tetrahydrofuran; phosphate buffer; ethanol;
DOI:10.1021/ol035101r