tert-butyl (4S)-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-(((4-nitrophenoxy)carbonyl)oxy)-2-oxoethyl)phenyl)amino)-5-oxopentanoate

Base Information

Chemical Name:tert-butyl (4S)-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-(((4-nitrophenoxy)carbonyl)oxy)-2-oxoethyl)phenyl)amino)-5-oxopentanoate
CAS No.:1316833-11-0
Molecular Formula:C₄₄H₄₄N₄O₁₃
Molecular Weight:836.852
Hs Code.:

tert-butyl (4S)-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-(((4-nitrophenoxy)carbonyl)oxy)-2-oxoethyl)phenyl)amino)-5-oxopentanoate

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Chemical Property of tert-butyl (4S)-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-(((4-nitrophenoxy)carbonyl)oxy)-2-oxoethyl)phenyl)amino)-5-oxopentanoate

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Technology Process of tert-butyl (4S)-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-(((4-nitrophenoxy)carbonyl)oxy)-2-oxoethyl)phenyl)amino)-5-oxopentanoate

There total 11 articles about tert-butyl (4S)-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-(((4-nitrophenoxy)carbonyl)oxy)-2-oxoethyl)phenyl)amino)-5-oxopentanoate 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: 39.9%

: 1316833-02-9
tert-butyl (4S)-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-hydroxy-2-oxoethyl)phenyl)amino)-5-oxopentanoate

: 7693-46-1
4-Nitrophenyl chloroformate

: 1316833-11-0
tert-butyl (4S)-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-(((4-nitrophenoxy)carbonyl)oxy)-2-oxoethyl)phenyl)amino)-5-oxopentanoate

Guidance literature:: With pyridine; dmap; In dichloromethane; at 0 ℃; for 24h;
DOI:10.1021/ja200808y

Reference yield:

: 1316832-28-6
allyl 2-(2-hydroxy-2-(4-nitrophenyl)acetamido)acetate

: 1316833-11-0
tert-butyl (4S)-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-(((4-nitrophenoxy)carbonyl)oxy)-2-oxoethyl)phenyl)amino)-5-oxopentanoate

Guidance literature:: Multi-step reaction with 3 steps

1: acetic acid; zinc / tetrahydrofuran / 2 h / 20 °C

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere

3: pyridine; dmap / dichloromethane / 24 h / 0 °C

With pyridine; dmap; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja200808y

Reference yield:

: 138646-99-8
tert-butyl 2-bromo-2-(4-nitrophenyl)acetate

: 1316833-11-0
tert-butyl (4S)-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-((4-(2-((2-(allyloxy)-2-oxoethyl)amino)-1-(((4-nitrophenoxy)carbonyl)oxy)-2-oxoethyl)phenyl)amino)-5-oxopentanoate

Guidance literature:: Multi-step reaction with 7 steps

1: water; N,N-dimethyl-formamide / 3 h / 100 °C / Inert atmosphere

2: trifluoroacetic acid / dichloromethane / 8 h

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere

4: caesium carbonate; allyl alcohol

5: acetic acid; zinc / tetrahydrofuran / 2 h / 20 °C

6: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C / Inert atmosphere

7: pyridine; dmap / dichloromethane / 24 h / 0 °C

With pyridine; dmap; caesium carbonate; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; allyl alcohol; trifluoroacetic acid; zinc; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ja200808y