(2S,4R)-1-((S)-2-(tert-butyl)-4-oxo-7,10,13-trioxa-3-azahexadec-15-yn-1-oyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

Base Information

• Chemical Name: (2S,4R)-1-((S)-2-(tert-butyl)-4-oxo-7,10,13-trioxa-3-azahexadec-15-yn-1-oyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide
• CAS No.: 2374122-30-0
• Molecular Formula: C₃₂H₄₄N₄O₇S
• Molecular Weight: 628.79
• Mol file: 2374122-30-0.mol

Synonyms:

Chemical Property of (2S,4R)-1-((S)-2-(tert-butyl)-4-oxo-7,10,13-trioxa-3-azahexadec-15-yn-1-oyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

(S,R,S)-AHPC-PEG3-Alkyne ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Protein degrader builiding block (S,R,S)-AHPC-PEG4-Alkyne enables the synthesis of molecules for targeted protein degradation and PROTAC (proteolysis-targeting chimeras) technology. This conjugate contains a von Hippel-Lindau (VHL)-recruiting ligand and a PEGylated crosslinker with pendant alkyne for click chemistry with an azide on the target ligand. Because even slight alterations in ligands and crosslinkers can affect ternary complex formation between the target, E3 ligase, and PROTAC, many analogs are prepared to screen for optimal target degradation. When used with other protein degrader building blocks with a pendant alkyne group, parallel synthesis can be used to more quickly generate PROTAC libraries that feature variation in crosslinker length, composition, and E3 ligase ligand.

Technology Process of (2S,4R)-1-((S)-2-(tert-butyl)-4-oxo-7,10,13-trioxa-3-azahexadec-15-yn-1-oyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide

There total 1 articles about (2S,4R)-1-((S)-2-(tert-butyl)-4-oxo-7,10,13-trioxa-3-azahexadec-15-yn-1-oyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide 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: 32.0%

3-(2-(2-(prop-2-yn-1-yloxy)ethoxy)ethoxy)propanoic acid (1347760-82-0,1421676-62-1) + (2S,4R)-1-[(2S)-2-amino-3,3-dimethylbutanoyl]-4-hydroxy-N-{[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl}pyrrolidine-2-carboxamide hydrochloride (1448189-80-7,2115897-23-7) → (2S,4R)-1-((S)-2-(tert-butyl)-4-oxo-7,10,13-trioxa-3-azahexadec-15-yn-1-oyl)-4-hydroxy-N-(4-(4-methylthiazol-5-yl)benzyl)pyrrolidine-2-carboxamide (2374122-30-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 25 ℃; for 1h;

DOI:10.1021/acsmedchemlett.9b00219

upstream raw materials:

3-(2-(2-(prop-2-yn-1-yloxy)ethoxy)ethoxy)propanoic acid

(2S,4R)-1-[(2S)-2-amino-3,3-dimethylbutanoyl]-4-hydroxy-N-{[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methyl}pyrrolidine-2-carboxamide hydrochloride