(2S,3S)-ethyl-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-phenylpropanoate

Base Information

• Chemical Name: (2S,3S)-ethyl-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-phenylpropanoate
• CAS No.: 1116503-92-4
• Molecular Formula: C₁₆H₂₃NO₅
• Molecular Weight: 309.362
• Mol file: 1116503-92-4.mol

Synonyms:(2S,3S)-ethyl-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-phenylpropanoate

Chemical Property of (2S,3S)-ethyl-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-phenylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-ethyl-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-phenylpropanoate

There total 7 articles about (2S,3S)-ethyl-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: 100.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S,3S)-ethyl 2-azido-3-hydroxy-3-phenylpropanoate (1116503-90-2) → (2S,3S)-ethyl-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-phenylpropanoate (1116503-92-4)

Guidance literature:

With 5%-palladium/activated carbon; hydrogen; In ethyl acetate; at 20 ℃;

DOI:10.1016/j.tet.2018.09.011

Reference yield:

ethyl-2-((tert-butoxycarbonyl)amino)-3-oxo-3-phenylpropanoate (151870-52-9) → (2S,3S)-ethyl-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-phenylpropanoate (1116503-92-4) + C16H23NO5 (1294479-58-5)

Guidance literature:

With dichloro(benzene)ruthenium(II) dimer; formic acid; (1R,2R)-pseudoephedrine; triethylamine; In isopropyl alcohol; optical yield given as %ee;

DOI:10.1016/j.tetlet.2011.01.146

Reference yield:

ethyl cinnamate (4192-77-2) → (2S,3S)-ethyl-2-((tert-butoxycarbonyl)amino)-3-hydroxy-3-phenylpropanoate (1116503-92-4)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium osmate; potassium hexacyanoferrate(III); hydroquinidein 1,4-phthalazinediyl diether; potassium carbonate; methanesulfonamide / water; tert-butyl alcohol / 15 h / 0 °C

2: triethylamine / dichloromethane / 3 h / -20 - -10 °C

3: sodium azide / N,N-dimethyl-formamide / 8 h / 55 °C

4: hydrogen; 5%-palladium/activated carbon / ethyl acetate / 20 °C

With potassium osmate; sodium azide; methanesulfonamide; 5%-palladium/activated carbon; hydrogen; potassium carbonate; hydroquinidein 1,4-phthalazinediyl diether; triethylamine; potassium hexacyanoferrate(III); In dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1016/j.tet.2018.09.011

upstream raw materials:

ethyl-2-((tert-butoxycarbonyl)amino)-3-oxo-3-phenylpropanoate

di-tert-butyl dicarbonate

(2S,3S)-ethyl 2-azido-3-hydroxy-3-phenylpropanoate

benzaldehyde