(2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxy-3-phenylpropanoate

Base Information

Chemical Name:(2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxy-3-phenylpropanoate
CAS No.:1346156-35-1
Molecular Formula:C₁₉H₂₈N₂O₆
Molecular Weight:380.441
Hs Code.:

Synonyms:(2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxy-3-phenylpropanoate

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Chemical Property of (2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxy-3-phenylpropanoate

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Technology Process of (2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxy-3-phenylpropanoate

There total 1 articles about (2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxy-3-phenylpropanoate 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: 77.0%

: 15761-38-3
L-N-Boc-Ala

: 911475-69-9
(2S,3R)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester

: 1346156-35-1
(2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxy-3-phenylpropanoate

Guidance literature:: L-N-Boc-Ala; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; Inert atmosphere;

(2S,3R)-2-amino-3-hydroxy-3-phenyl-propionic acid ethyl ester; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1016/j.tetasy.2011.08.026

Reference yield: 86.0%

: 1346156-35-1
(2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxy-3-phenylpropanoate

: 74-88-4
methyl iodide

: 1345116-55-3
(2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-methoxy-3-phenylpropanoate

Guidance literature:: With silver(l) oxide; In tetrahydrofuran; at 45 ℃; for 48h; Inert atmosphere; Darkness;
DOI:10.1016/j.tetasy.2011.08.026

Reference yield:

: 1346156-35-1
(2S,3R)-ethyl 2-((S)-2-(tert-butoxycarbonylamino)propanamido)-3-hydroxy-3-phenylpropanoate

: C₂₆H₄₁N₃O₈

Guidance literature:: Multi-step reaction with 6 steps

1.1: silver(l) oxide / tetrahydrofuran / 48 h / 45 °C / Inert atmosphere; Darkness

2.1: trifluoroacetic acid / dichloromethane / 0 - 20 °C / Inert atmosphere

3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0 °C / Inert atmosphere

3.2: 24 h / 20 °C / Inert atmosphere

4.1: lithium hydroxide / tetrahydrofuran; water / 2 h / 0 °C / Inert atmosphere

4.2: Inert atmosphere; Saturated solution

5.1: diethyl ether / 0.33 h / 0 °C / Inert atmosphere

6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; silver(l) oxide; lithium hydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; water;
DOI:10.1016/j.tetasy.2011.08.026