t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-4-phenyl-(2S)-butanoate

Base Information

Chemical Name:t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-4-phenyl-(2S)-butanoate
CAS No.:123975-51-9
Molecular Formula:C₂₄H₂₉NO₇
Molecular Weight:443.497
Hs Code.:

Synonyms:t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-4-phenyl-(2S)-butanoate

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Chemical Property of t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-4-phenyl-(2S)-butanoate

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Technology Process of t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-4-phenyl-(2S)-butanoate

There total 10 articles about t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-4-phenyl-(2S)-butanoate 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: 50.0%

: 60079-12-1
β-Methyl α-tert-butyl (2S)-N-(benzyloxycarbonyl)aspartate

: 100-52-7
benzaldehyde

: 123975-51-9
t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-4-phenyl-(2S)-butanoate

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; further reagent;

Reference yield:

: 100-52-7
benzaldehyde

: 127605-37-2
α-t-butyl β-methyl N-Z-(RS)-aspartate

: 123975-51-9,127643-77-0,127643-78-1,127643-81-6,127643-82-7
t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-4-phenyl-(2RS)-butanoate

Guidance literature:: With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃;

Reference yield:

: 501-53-1,94274-21-2
benzyl chloroformate

: 123975-51-9
t-butyl 2-benzyloxycarbonylamino-3-carbomethoxy-4-hydroxy-4-phenyl-(2S)-butanoate

Guidance literature:: Multi-step reaction with 5 steps

1: 77 percent / potassium carbonate / H₂O; diethyl ether / 4 h / Ambient temperature

2: 95 percent / conc. sulphuric acid / CH₂Cl₂ / 48 h / Ambient temperature

3: 84 percent / tetrakis(triphenylphosphine)-palladium⁽⁰⁾, triphenylphosphine, pyrrolidine / CH₂Cl₂ / 0.17 h / Ambient temperature

4: 69 percent / diethyl ether / 1 h / Ambient temperature

5: 1.) bis(trimethylsilyl)amine, BuLi / 1.) THF, r.t., 10 min; 2.) THF, -30 - -40 deg C, 45 min; 3.) -78 deg C, 15 min

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sulfuric acid; potassium carbonate; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; In diethyl ether; dichloromethane; water;
DOI:10.1016/S0040-4020(01)85141-3