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Azido-PEG1-methyl ester - CAS 1835759-80-2

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Azido-PEG1-methyl ester is a polyethylene glycol (PEG)-based PROTAC linker. Azido-PEG1-methyl ester can be used in the synthesis of a series of PROTACs.

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Molecular Formula

C₆H₁₁N₃O₃

Molecular Weight

173.17

Azido-PEG1-methyl 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
    
    methyl 3-(2-azidoethoxy)propanoate
    
    Synonyms
    
    methyl 3-(2-azidoethoxy)propanoate; Propanoic acid, 3-(2-azidoethoxy)-, methyl ester
- Properties
  - InChI Key
    
    LAQALTVGFQMCEV-UHFFFAOYSA-N
    
    InChI
    
    InChI=1S/C6H11N3O3/c1-11-6(10)2-4-12-5-3-8-9-7/h2-5H2,1H3
    
    Canonical SMILES
    
    COC(=O)CCOCCN=[N+]=[N-]
- Reference Reading
  - 1. Novel azido fatty acid ester derivatives from conjugated C(18) enynoate
    
    M S Lie Ken Jie, M S Alam Chem Phys Lipids. 2001 May;111(1):29-35.doi: 10.1016/s0009-3084(01)00140-2.
    
    Methyl octadec-11Z-en-9-ynoate (1) was epoxidized to give methyl 11,12-Z-epoxy-octadec-9-ynoate (2, 81%). Acid catalyzed ring opening of the epoxy ring of compound 2 gave methyl 11,12-dihydroxy-octadec-9-ynoate (3, 80%). The latter was treated with mesyl chloride to yield methyl 11,12-dimesyloxy-octadec-9-ynoate (4, 76%). Reaction of compound 4 with sodium azide furnished methyl 11-azido-12-mesyloxy-octadec-9-ynoate (5a, 49%) and methyl 11-azido-octadec-11E-en-9-ynoate (5b, 24%). Compound 2 was semi-hydrogenated over Lindlar catalyst to give methyl 11,12-Z-epoxy-octadec-9Z-enoate (6, 90%). This allylic epoxy fatty ester (6) was reacted with sodium azide to give a mixture of methyl 11-azido-12-hydroxy-octadec-9Z-enoate (7a) and methyl 9-azido-12-hydroxy-octadec-9E-enoate (7b), which could not be separated into individual components by silica chromatography. Chromic acid oxidation of the mixture of compounds 7a and 7b furnished methyl 9-azido-12-oxo-octadec-10E-enoate (8, 42% based on amount of compound 6 used) and an intractable mixture of polar compounds. The various products were characterized by NMR spectroscopic and mass spectral analyses.

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It is commonly abbreviated as: C₁V₁ = C₂V₂

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