tert-butyl (2S,3R)-2-[(tert-butoxycarbonyl)amino]-3-hydroxy-3-phenylpropanoate

Base Information

Chemical Name:tert-butyl (2S,3R)-2-[(tert-butoxycarbonyl)amino]-3-hydroxy-3-phenylpropanoate
CAS No.:78029-00-2
Molecular Formula:C₁₈H₂₇NO₅
Molecular Weight:337.416
Hs Code.:

Synonyms:

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Chemical Property of tert-butyl (2S,3R)-2-[(tert-butoxycarbonyl)amino]-3-hydroxy-3-phenylpropanoate

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Technology Process of tert-butyl (2S,3R)-2-[(tert-butoxycarbonyl)amino]-3-hydroxy-3-phenylpropanoate

There total 14 articles about tert-butyl (2S,3R)-2-[(tert-butoxycarbonyl)amino]-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: 59.0%

: 1454771-48-2
(4S,5R)-5-phenyl-4-(tert-butoxycarbonyl)-N⁽³⁾-(tert-butoxycarbonyl)oxazolidin-2-one

: 78029-00-2,78043-76-2
tert-butyl (2S,3R)-2-[(tert-butoxycarbonyl)amino]-3-hydroxy-3-phenylpropanoate

Guidance literature:: With water; lithium hydroxide; In 1,4-dioxane; at 20 ℃; for 0.75h;
DOI:10.1016/j.tet.2013.08.007

Reference yield:

: 14990-09-1
tert-butyl cinnamate

: 78029-00-2,78043-76-2
tert-butyl (2S,3R)-2-[(tert-butoxycarbonyl)amino]-3-hydroxy-3-phenylpropanoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / -78 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

1.3: 15 h / 20 °C / Inert atmosphere

2.1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethyl acetate / 15 h / 20 °C / 3800.26 Torr

3.1: triethylamine; dmap / dichloromethane / 15 h / 20 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 15 h / 20 °C

5.1: trichloroacetic acid / dichloromethane / 15 h / 20 °C / Inert atmosphere

6.1: triethylamine; dmap / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

7.1: water; lithium hydroxide / 1,4-dioxane / 0.75 h / 20 °C

With dmap; n-butyllithium; 10 wt% Pd(OH)2 on carbon; tetrabutyl ammonium fluoride; water; hydrogen; triethylamine; lithium hydroxide; trichloroacetic acid; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; ethyl acetate;
DOI:10.1016/j.tet.2013.08.007

Reference yield:

: 151671-03-3
tert-butyl (2R,3R,αR)-3--2-hydroxy-3-phenylpropionate

: 78029-00-2,78043-76-2
tert-butyl (2S,3R)-2-[(tert-butoxycarbonyl)amino]-3-hydroxy-3-phenylpropanoate

Guidance literature:: Multi-step reaction with 6 steps

1: 10 wt% Pd(OH)2 on carbon; hydrogen / ethyl acetate / 15 h / 20 °C / 3800.26 Torr

2: triethylamine; dmap / dichloromethane / 15 h / 20 °C / Inert atmosphere

3: sodium hydride / N,N-dimethyl-formamide; mineral oil / 3 h / 50 °C

4: trichloroacetic acid / dichloromethane / 15 h / 20 °C / Inert atmosphere

5: triethylamine; dmap / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

6: water; lithium hydroxide / 1,4-dioxane / 0.75 h / 20 °C

With dmap; 10 wt% Pd(OH)2 on carbon; water; hydrogen; sodium hydride; triethylamine; lithium hydroxide; trichloroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; mineral oil;
DOI:10.1016/j.tet.2013.08.007