Azido-PEG9-t-butyl ester

 CAS No.: 1818294-43-7  Cat No.: BP-501381  Purity: >95% 4.5  

Azido-PEG9-t-butyl ester is a heterobifunctional polyethylene glycol linker featuring an azide handle at one terminus and a protected carboxylate as a t-butyl ester at the other. The PEG segment provides a flexible, hydrophilic spacer that can reduce steric interference and improve effective reach between the warhead-binding moiety and the E3-ligase recruiting ligand in PROTAC constructs. The terminal azide enables chemoselective conjugation via copper-free or copper-catalyzed azide–alkyne cycloaddition, facilitating robust attachment to alkyne-functional partners under conditions commonly used for PROTAC synthesis. The t-butyl ester serves as an acid-labile protecting group that can be removed to reveal a carboxylic acid for subsequent coupling to amine- or hydroxyl-bearing components, allowing modular assembly and late-stage functionalization. This linker is valuable for researchers optimizing linker length, solubility, and conjugation strategy to tune targeted protein degradation performance.

Azido-PEG9-t-butyl ester

Structure of 1818294-43-7

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Category
PROTAC Linker
Molecular Formula
C25H49N3O11
Molecular Weight
567.67
Appearance
Pale Yellow Oily Liquid

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

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Purity
>95%
Solubility
Soluble in DMSO
Appearance
Pale Yellow Oily Liquid
Storage
Store at 2-8°C for short term (days to weeks) or -20°C for long term (months to years)
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl 3-[2-[2-[2-[2-[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
Azido-PEG9-Boc; tert-butyl 1-azido-3,6,9,12,15,18,21,24,27-nonaoxatriacontan-30-oate; 4,7,10,13,16,19,22,25,28-Nonaoxatriacontanoic acid, 30-azido-, 1,1-dimethylethyl ester; 2-Methyl-2-propanyl 1-azido-3,6,9,12,15,18,21,24,27-nonaoxatriacontan-30-oate; 3,6,9,12,15,18,21,24,27-Nonaoxatriacontan-30-oic acid, 1-azido-, 1,1-dimethylethyl ester
InChI Key
HNZVYHQBKFTIJZ-UHFFFAOYSA-N
InChI
InChI=1S/C25H49N3O11/c1-25(2,3)39-24(29)4-6-30-8-10-32-12-14-34-16-18-36-20-22-38-23-21-37-19-17-35-15-13-33-11-9-31-7-5-27-28-26/h4-23H2,1-3H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCOCCOCCOCCOCCOCCOCCN=[N+]=[N-]

Azido-PEG9-t-butyl ester is a PEG-based linker designed for modular synthesis of PROTACs, enabling efficient conjugation between a ligand and an E3-recruiting or targeting moiety. Its azide handle supports bioorthogonal “click” coupling strategies, while the protected ester functionality offers controlled functional-group reactivity during assembly. These features help researchers build well-defined conjugates with tunable spacing and improved synthetic flexibility; detailed structural and reactivity considerations are provided below.

Structure: The linker contains an azide functional group attached to a polyethylene glycol chain, terminating in a tert-butyl ester. It combines ether-rich PEG segments with an ester carbonyl and an azide, providing conformational flexibility and chemical stability under non-deprotection conditions.

Reactivity: The azide can participate in copper-catalyzed azide–alkyne cycloaddition to form stable triazole linkages, typically using Cu(I) generated in situ and an appropriate alkyne partner. The tert-butyl ester is commonly deprotected under acid conditions to yield a carboxylic acid for subsequent amide or other coupling reactions. Solvent choice and temperature should be optimized to preserve sensitive PROTAC ligands.

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L

* 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

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
g/mol
g

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