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Azido-PEG3-O-NHS ester - CAS 2110448-98-9

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Azido-PEG3-O-NHS ester is a polyethylene glycol (PEG)-based PROTAC linker. Azido-PEG3-O-NHS ester can be used in the synthesis of a series of PROTACs.

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Molecular Formula

C₁₃H₂₀N₄O₈

Molecular Weight

360.32

Azido-PEG3-O-NHS ester

- Specification
  - Purity
    
    98%
    
    Storage
    
    Please store the product under the recommended conditions in the Certificate of Analysis.
    
    Shipping
    
    Room temperature in continental US; may vary elsewhere.
    
    IUPAC Name
    
    2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethyl (2,5-dioxopyrrolidin-1-yl) carbonate
    
    Synonyms
    
    Azido-PEG3-succinimidyl carbonate
- Properties
  - InChI Key
    
    RIGURCMIYKOKGN-UHFFFAOYSA-N
    
    InChI
    
    InChI=1S/C13H20N4O8/c14-16-15-3-4-21-5-6-22-7-8-23-9-10-24-13(20)25-17-11(18)1-2-12(17)19/h1-10H2
    
    Canonical SMILES
    
    C1CC(=O)N(C1=O)OC(=O)OCCOCCOCCOCCN=[N+]=[N-]
- Reference Reading
  - 1. Photochemically-Mediated, Nickel-Catalyzed Synthesis of N-(Hetero)aryl Sulfamate Esters
    
    J Miles Blackburn, Anastasia L Gant Kanegusuku, Georgia E Scott, Jennifer L Roizen Org Lett. 2019 Sep 6;21(17):7049-7054.doi: 10.1021/acs.orglett.9b02621.Epub 2019 Aug 22.
    
    A general method is described for the coupling of (hetero)aryl bromides with O-alkyl sulfamate esters. The protocol relies on catalytic amounts of nickel and photoexcitable iridium complexes and proceeds under visible light irradiation at ambient temperature. This technology engages a broad range of simple and complex O-alkyl sulfamate ester substrates under mild conditions. Furthermore, it is possible to avoid undesirable N-alkylation, which was found to plague palladium-based protocols for N-arylation of O-alkyl sulfamate esters. These investigations represent the first use of sulfamate esters as nucleophiles in transition metal-catalyzed C-N coupling processes.

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