N^α-[[4-[(benzyloxycarbonyl)methylamino]benzoyl]-L-(α-benzyloxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide

Base Information

• Chemical Name: N^α-[[4-[(benzyloxycarbonyl)methylamino]benzoyl]-L-(α-benzyloxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide
• CAS No.: 511545-18-9
• Molecular Formula: C₈₂H₁₃₀N₄O₁₃
• Molecular Weight: 1379.95

Synonyms:N^α-[[4-[(benzyloxycarbonyl)methylamino]benzoyl]-L-(α-benzyloxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide

Chemical Property of N^α-[[4-[(benzyloxycarbonyl)methylamino]benzoyl]-L-(α-benzyloxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide

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Technology Process of N^α-[[4-[(benzyloxycarbonyl)methylamino]benzoyl]-L-(α-benzyloxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide

There total 7 articles about N^α-[[4-[(benzyloxycarbonyl)methylamino]benzoyl]-L-(α-benzyloxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide 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: 77.0%

N-<4-<<(benzyloxy)carbonyl>methylamino>benzoyl>-L-glutamic acid α-benzyl ester (79974-14-4) + N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide (167986-17-6) → Nα-[[4-[(benzyloxycarbonyl)methylamino]benzoyl]-L-(α-benzyloxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide (511545-18-9)

Guidance literature:

N-<4-<<(benzyloxy)carbonyl>methylamino>benzoyl>-L-glutamic acid α-benzyl ester; With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In dichloromethane; for 3h;

N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide; With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 21h; pH=8;

DOI:10.1071/CH02125

Reference yield: 68.0%

benzyl (4-(chlorocarbonyl)phenyl)(methyl)carbamate (66891-86-9) + Nα-[L-(α-benzyloxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide (511545-15-6) → Nα-[[4-[(benzyloxycarbonyl)methylamino]benzoyl]-L-(α-benzyloxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide (511545-18-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1071/CH02125

Reference yield:

N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]-Nα-(benzyloxycarbonyl)glycinamide (137247-67-7) → Nα-[[4-[(benzyloxycarbonyl)methylamino]benzoyl]-L-(α-benzyloxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide (511545-18-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / H₂ / Pd/C / ethanol; ethyl acetate / 20 h / 40 °C

2: 91 percent / DCC; DMAP / CH₂Cl₂ / 0.31 h / 20 °C

3: 100 percent / TFA / CH₂Cl₂ / 2.5 h / 20 °C

4: 68 percent / (i-Pr)2NEt / CH₂Cl₂ / 0 - 20 °C

With dmap; hydrogen; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; ethyl acetate;

DOI:10.1071/CH02125

upstream raw materials:

benzyl (4-(chlorocarbonyl)phenyl)(methyl)carbamate

N^α-[L-(α-benzyloxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide

N-<4-<<(benzyloxy)carbonyl>methylamino>benzoyl>-L-glutamic acid α-benzyl ester

N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide

Downstream raw materials:

N^α-[(4-methylamino)benzoyl-L-γ-glutamyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide

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