N^α-[[4-[(benzyloxycarbonyl)methylamino]benzoyl]-L-(α-tert-butoxy)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-tert-butoxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide
• CAS No.: 511545-04-3
• Molecular Formula: C₇₉H₁₃₂N₄O₁₃
• Molecular Weight: 1345.94

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

Chemical Property:

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

There total 4 articles about N^α-[[4-[(benzyloxycarbonyl)methylamino]benzoyl]-L-(α-tert-butoxy)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: 58.0%

α-tert-butyl N-[4-(N-benzyloxycarbonyl-N-methyl)aminobenzoyl]-L-glutamate (511544-85-7) + N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide (167986-17-6) → Nα-[[4-[(benzyloxycarbonyl)methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide (511545-04-3)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 24h;

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-tert-butoxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide (511545-04-3)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 58 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

With dmap; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; dichloromethane; ethyl acetate;

DOI:10.1071/CH02125

Reference yield:

4-<<(benzyloxy)carbonyl>methylamino>benzoic acid (2528-30-5) → Nα-[[4-[(benzyloxycarbonyl)methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide (511545-04-3)

Guidance literature:

Multi-step reaction with 3 steps

1: SOCl₂ / toluene / 4 h / Heating

2: 99 percent / (i-Pr)2NEt / dioxane; H₂O / 0 - 20 °C

3: 58 percent / DCC; DMAP / CH₂Cl₂ / 24 h / 20 °C

With dmap; thionyl chloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane; water; toluene;

DOI:10.1071/CH02125

upstream raw materials:

α-tert-butyl N-[4-(N-benzyloxycarbonyl-N-methyl)aminobenzoyl]-L-glutamate

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

4-<<(benzyloxy)carbonyl>methylamino>benzoic acid

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

Downstream raw materials:

N^α-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-(α-tert-butoxy)glutamoyl]-N-[2-[(1-oxohexadecyl)oxy]-1,1-bis[[(1-oxohexadecyl)oxy]methyl]ethyl]glycinamide

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

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