N^α-[N-(benzyloxycarbonyl)-L-(α-benzyloxy)glutamoyl]-N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycinamide

Base Information

• Chemical Name: N^α-[N-(benzyloxycarbonyl)-L-(α-benzyloxy)glutamoyl]-N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycinamide
• CAS No.: 511545-41-8
• Molecular Formula: C₂₆H₃₃N₃O₉
• Molecular Weight: 531.563

Synonyms:N^α-[N-(benzyloxycarbonyl)-L-(α-benzyloxy)glutamoyl]-N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycinamide

Chemical Property of N^α-[N-(benzyloxycarbonyl)-L-(α-benzyloxy)glutamoyl]-N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycinamide

Chemical Property:

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Technology Process of N^α-[N-(benzyloxycarbonyl)-L-(α-benzyloxy)glutamoyl]-N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycinamide

There total 1 articles about N^α-[N-(benzyloxycarbonyl)-L-(α-benzyloxy)glutamoyl]-N-[2-hydroxy-1,1-bis(hydroxymethyl)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: 65.0%

Cbz-(L)-Glu-OBn (3705-42-8) + N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycinamide (159339-55-6) → Nα-[N-(benzyloxycarbonyl)-L-(α-benzyloxy)glutamoyl]-N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycinamide (511545-41-8)

Guidance literature:

Cbz-(L)-Glu-OBn; With 1-hydroxy-pyrrolidine-2,5-dione; dicyclohexyl-carbodiimide; In acetonitrile; at 20 ℃; for 3.5h;

N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycinamide; With triethylamine; In N,N-dimethyl-formamide; acetonitrile; at 20 ℃; pH=8;

DOI:10.1071/CH02125

Reference yield:

Nα-[N-(benzyloxycarbonyl)-L-(α-benzyloxy)glutamoyl]-N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycinamide (511545-41-8) → Nα-[[4-[[(2,4-diamino-6-pteridinyl)methyl]methylamino]benzoyl]-L-γ-glutamyl]-N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycinamide

Guidance literature:

Multi-step reaction with 2 steps

1.1: 100 percent / H₂ / Pd/C / ethanol

2.1: Et₃N; TPTU / dimethylformamide / 2 h / 20 °C

2.2: 52 percent / Et₃N / dimethylformamide

With hydrogen; O-(1,2-dihydro-2-oxo-1-pyridyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1071/CH02125

upstream raw materials:

Cbz-(L)-Glu-OBn

N-[2-hydroxy-1,1-bis(hydroxymethyl)ethyl]glycinamide

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