tert-butyl 3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(4-(2-(2-(allyloxy)-2-oxoethylamino)-1-hydroxy-2-oxoethyl)phenylamino)-4-oxobutanoate

Base Information

• Chemical Name: tert-butyl 3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(4-(2-(2-(allyloxy)-2-oxoethylamino)-1-hydroxy-2-oxoethyl)phenylamino)-4-oxobutanoate
• CAS No.: 1316832-32-2
• Molecular Formula: C₃₆H₃₉N₃O₉
• Molecular Weight: 657.72

Synonyms:tert-butyl 3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(4-(2-(2-(allyloxy)-2-oxoethylamino)-1-hydroxy-2-oxoethyl)phenylamino)-4-oxobutanoate

Chemical Property of tert-butyl 3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(4-(2-(2-(allyloxy)-2-oxoethylamino)-1-hydroxy-2-oxoethyl)phenylamino)-4-oxobutanoate

Chemical Property:

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Technology Process of tert-butyl 3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(4-(2-(2-(allyloxy)-2-oxoethylamino)-1-hydroxy-2-oxoethyl)phenylamino)-4-oxobutanoate

There total 10 articles about tert-butyl 3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(4-(2-(2-(allyloxy)-2-oxoethylamino)-1-hydroxy-2-oxoethyl)phenylamino)-4-oxobutanoate 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: 74.8%

allyl 2-(4-(aminophenyl)-2-hydroxyacetamido)acetate (1316832-30-0) + Fmoc-(tBu)Asp-OH (71989-14-5) → tert-butyl 3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(4-(2-(2-(allyloxy)-2-oxoethylamino)-1-hydroxy-2-oxoethyl)phenylamino)-4-oxobutanoate (1316832-32-2)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/ja200808y

Reference yield:

tert-butyl 2-bromo-2-(4-nitrophenyl)acetate (138646-99-8) → tert-butyl 3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(4-(2-(2-(allyloxy)-2-oxoethylamino)-1-hydroxy-2-oxoethyl)phenylamino)-4-oxobutanoate (1316832-32-2)

Guidance literature:

Multi-step reaction with 6 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

With 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

Reference yield:

allyl 2-(2-hydroxy-2-(4-nitrophenyl)acetamido)acetate (1316832-28-6) → tert-butyl 3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(4-(2-(2-(allyloxy)-2-oxoethylamino)-1-hydroxy-2-oxoethyl)phenylamino)-4-oxobutanoate (1316832-32-2)

Guidance literature:

Multi-step reaction with 2 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

With dmap; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja200808y

upstream raw materials:

tert-butyl 2-bromo-2-(4-nitrophenyl)acetate

allyl 2-(2-acetoxy-2-(4-nitrophenyl)acetamido)acetate

allyl 2-(2-hydroxy-2-(4-nitrophenyl)acetamido)acetate

allyl 2-(4-(aminophenyl)-2-hydroxyacetamido)acetate

Downstream raw materials:

(E)-allyl 9-(4-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-tert-butoxy-4-oxobutanamido)phenyl)-1-(4-((4-(dimethylamino)phenyl)diazenyl)phenyl)-1,7,10-trioxo-8-oxa-2,6,11-triazatridecan-13-oate

(E)-9-(4-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-tert-butoxy-4-oxobutanamido)phenyl)-1-(4-((4-(dimethylamino)phenyl)diazenyl)phenyl)-1,7,10-trioxo-8-oxa-2,6,11-triazatridecan-13-oic acid

tert-butyl 3-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(4-(2-(2-(allyloxy)-2-oxoethylamino)-1-((4-nitrophenoxy)carbonyloxy)-2-oxoethyl)phenylamino)-4-oxobutanoate

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