Azido-PEG1-t-butyl ester

 CAS No.: 1374658-85-1  Cat No.: BP-500997  Purity: >95% 4.5  

Azido-PEG1-t-butyl ester is a short, PEG-based linker bearing a terminal azide for efficient bioorthogonal conjugation and a protected t-butyl ester that can be selectively unmasked under appropriate conditions to reveal a carboxylate handle. Structurally, it provides a compact ethylene glycol segment that imparts modest hydrophilicity and conformational flexibility while keeping the reactive termini separated from bulky warheads. In PROTAC and targeted protein degradation workflows, the azide functionality enables reliable attachment to complementary alkyne-bearing partners via copper-free click chemistry, allowing researchers to assemble degraders with defined connectivity and minimal side reactions. The t-butyl ester protection supports controlled synthetic sequencing, facilitating late-stage coupling or incorporation into larger architectures. This linker is valuable for constructing PROTACs where short-range spacing and robust, orthogonal functional-group compatibility are required to optimize ternary complex formation and degradation efficiency.

Azido-PEG1-t-butyl ester

Structure of 1374658-85-1

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Category
PROTAC Linker
Molecular Formula
C9H17N3O3
Molecular Weight
215.25
Appearance
Pale Yellow or Colorless Oily Liquid

* For research and manufacturing use only. Not for human or clinical use.

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Purity
>95%
Appearance
Pale Yellow or Colorless Oily Liquid
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl 3-(2-azidoethoxy)propanoate
Synonyms
Azido-PEG1-Boc; Propanoic acid, 3-(2-azidoethoxy)-, 1,1-dimethylethyl ester; N3-PEG1-t-butyl ester; 2-Methyl-2-propanyl 3-(2-azidoethoxy)propanoate
InChI Key
YQLWGRGAPJGNNQ-UHFFFAOYSA-N
InChI
InChI=1S/C9H17N3O3/c1-9(2,3)15-8(13)4-6-14-7-5-11-12-10/h4-7H2,1-3H3
SMILES
CC(C)(C)OC(=O)CCOCCN=[N+]=[N-]

Azido-PEG1-t-butyl ester is a versatile PROTAC linker building block designed to enable modular assembly of targeted protein degraders. Its azide handle supports bioorthogonal conjugation strategies, while the PEG spacer provides conformational flexibility to help tune ternary-complex formation. The t-butyl ester functionality offers a protected carboxyl equivalent that can be unmasked under controlled conditions, facilitating downstream coupling to ligands.

Structure: The molecule contains an azide functional group attached to a short polyethylene glycol segment and a tert-butyl ester protecting group. Key features include ether linkages within the PEG chain, an ester carbonyl, and an azide moiety suitable for click-type transformations. Overall polarity and solubility are enhanced by the PEG segment.

Reactivity: The azide enables azide–alkyne cycloaddition or other azide-compatible conjugation approaches commonly used in PROTAC synthesis. The tert-butyl ester can be removed by acid-mediated deprotection to generate a reactive carboxylate for subsequent amide or ester bond formation with ligand-derived nucleophiles. Typical workflows employ inert atmosphere handling for sensitive intermediates, with solvents such as polar aprotic media and standard coupling chemistries for carboxyl activation.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

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g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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