Nε-PalMitoyl-L-glutaMic Acid γ-SucciniMidyl-α-tert-butyl Ester

Base Information

• Chemical Name: Nε-PalMitoyl-L-glutaMic Acid γ-SucciniMidyl-α-tert-butyl Ester
• CAS No.: 204521-63-1
• Molecular Formula: C29H50N2O7
• Molecular Weight: 538.725
• Mol file: 204521-63-1.mol

Synonyms:Nε-PalMitoyl-L-glutaMic Acid Gamma-SucciniMidyl-Alpha-tert-butyl Ester;(2S)-5-[(2,5-Dioxo-1-pyrrolidinyl)oxy]-5-oxo-2-[(1-oxohexadecyl)amino]pentanoic Acid 1,1-Dimethylethyl Ester;N|A-Palmitoyl-Glu-|A-succinimidyl-|A-tert-butyl Ester;N|A-Palmitoyl-L-glutamic Acid |A-Succinimidyl-|A-tert-butyl Ester;N|A-Hexadecanoyl-L-glutamic Acid |A-t-Butyl-|A-2,5-dioxopyrrolidin-1-yl-diester;

Chemical Property of Nε-PalMitoyl-L-glutaMic Acid γ-SucciniMidyl-α-tert-butyl Ester

Chemical Property:

• Melting Point: 86.0 to 90.0 °C
• PKA: 14.40±0.46(Predicted)
• PSA: 119.08000
• Density: 1.08±0.1 g/cm3(Predicted)
• LogP: 6.01040
• Storage Temp.: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Solubility.: Chloroform (Slightly), Methanol (Slightly, Heated)

Purity/Quality:

99% ^*data from raw suppliers

Nε-Palmitoyl-L-glutamicAcidγ-Succinimidyl-α-tert-butylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Used in the preparation of lipophilic human glucagon-like peptide-1 derivatives with protracted action profiles. An antiobesity agent. Nε-PalMitoyl-L-glutaMic Acid γ-SucciniMidyl-α-tert-butyl Ester is used in the preparation of lipophilic human glucagon-like peptide-1 derivatives with protracted action profiles.

Technology Process of Nε-PalMitoyl-L-glutaMic Acid γ-SucciniMidyl-α-tert-butyl Ester

There total 5 articles about Nε-PalMitoyl-L-glutaMic Acid γ-SucciniMidyl-α-tert-butyl Ester 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: 90.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + L-glutamic acid, N-(1-oxohexadecyl)-, 1-(1,1-dimethylethyl) ester (536721-25-2) → Nα-hexadecanoyl-L-glutamic acid α-tert-butyl ester γ-succinimidyl ester (204521-63-1)

Guidance literature:

With diisopropyl-carbodiimide; In dichloromethane; at 20 - 30 ℃; for 4h;

Reference yield:

L-glutamic acid, N-(1-oxohexadecyl)-, 1-(1,1-dimethylethyl) ester (536721-25-2) + O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate (105832-38-0) → Nα-hexadecanoyl-L-glutamic acid α-tert-butyl ester γ-succinimidyl ester (204521-63-1)

Guidance literature:

With triethylamine; In dimethyl sulfoxide; at 20 ℃; for 2h;

Reference yield:

1-hexadecylcarboxylic acid (57-10-3) → Nα-hexadecanoyl-L-glutamic acid α-tert-butyl ester γ-succinimidyl ester (204521-63-1)

Guidance literature:

Multi-step reaction with 3 steps

1: diisopropyl-carbodiimide / dichloromethane; acetonitrile

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 48 h

3: diisopropyl-carbodiimide / dichloromethane; acetonitrile / 48 h

With N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide; In dichloromethane; acetonitrile;

DOI:10.1002/psc.2890

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

L-glutamic acid, N-(1-oxohexadecyl)-, 1-(1,1-dimethylethyl) ester

1-hexadecylcarboxylic acid

O-(N-succinimidyl)-N,N,N',N'-tetramethyluronium tetrafluoroborate

Refernces

• 1、 -. "IMPROVED PROCESSES FOR THE PREPARATION OF PEPTIDE INTERMEDIATES/MODIFIERS". Page/Page column 16. . Retrieved 2020/10/21.
• 2、 -. "Novel GLP-1 Analogues". Paragraph 0117-0118. . Retrieved 2019/10/20.