(2S,4S)-2-Acetylamino-4-benzyloxycarbonylamino-pentanoic acid tert-butyl ester

Base Information

Chemical Name:(2S,4S)-2-Acetylamino-4-benzyloxycarbonylamino-pentanoic acid tert-butyl ester
CAS No.:186828-04-6
Molecular Formula:C₁₉H₂₈N₂O₅
Molecular Weight:364.442
Hs Code.:

Synonyms:(2S,4S)-2-Acetylamino-4-benzyloxycarbonylamino-pentanoic acid tert-butyl ester

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Chemical Property of (2S,4S)-2-Acetylamino-4-benzyloxycarbonylamino-pentanoic acid tert-butyl ester

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Technology Process of (2S,4S)-2-Acetylamino-4-benzyloxycarbonylamino-pentanoic acid tert-butyl ester

There total 7 articles about (2S,4S)-2-Acetylamino-4-benzyloxycarbonylamino-pentanoic acid tert-butyl ester 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: 96.0%

: 108-24-7
acetic anhydride

: 186828-03-5
(2S,4S)-2-Amino-4-benzyloxycarbonylamino-pentanoic acid tert-butyl ester

: 186828-04-6
(2S,4S)-2-Acetylamino-4-benzyloxycarbonylamino-pentanoic acid tert-butyl ester

Guidance literature:: With dmap; diisopropylamine; In dichloromethane; for 16h;
DOI:10.1021/jo9615007

Reference yield:

: 119595-77-6
(2S,4S)-α-tert-butyl γ-methyl N-(9-(9-phenylfluorenyl))-4-methylglutamate

: 186828-04-6
(2S,4S)-2-Acetylamino-4-benzyloxycarbonylamino-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 77 percent / aq. LiOH / dioxane / 15 h / 65 °C

2: 99 percent / H₂ / Pd(OH)2/C / methanol; ethyl acetate / 18 h / 2585.7 Torr / Ambient temperature

3: 94 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 18 h / Ambient temperature

4: 1.) diphenyl phosphorazidate, Et₃N / 1.) C₆H₆, reflux, 1 h, 2.) C₆H₆, reflux, 16 h

5: 97 percent / hydrazine / methanol / 18 h

6: 96 percent / diisopropylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h

With dmap; lithium hydroxide; diphenyl phosphoryl azide; hydrogen; sodium carbonate; triethylamine; diisopropylamine; hydrazine; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo9615007

Reference yield:

: 119595-73-2
L-α-tert-butyl γ-methyl N-(9-(9-phenylfluorenyl))glutamate

: 186828-04-6
(2S,4S)-2-Acetylamino-4-benzyloxycarbonylamino-pentanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

2: 77 percent / aq. LiOH / dioxane / 15 h / 65 °C

3: 99 percent / H₂ / Pd(OH)2/C / methanol; ethyl acetate / 18 h / 2585.7 Torr / Ambient temperature

4: 94 percent / Na₂CO₃ / tetrahydrofuran; H₂O / 18 h / Ambient temperature

5: 1.) diphenyl phosphorazidate, Et₃N / 1.) C₆H₆, reflux, 1 h, 2.) C₆H₆, reflux, 16 h

6: 97 percent / hydrazine / methanol / 18 h

7: 96 percent / diisopropylamine, 4-(dimethylamino)pyridine / CH₂Cl₂ / 16 h

With dmap; lithium hydroxide; diphenyl phosphoryl azide; hydrogen; sodium carbonate; triethylamine; diisopropylamine; hydrazine; palladium dihydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate;
DOI:10.1021/jo9615007