Azido-PEG4-t-butyl acetate

 CAS No.: 864681-04-9  Cat No.: BP-500426  Purity: >98.0% 4.5  

Azido-PEG4-t-butyl acetate is a PEG-based, azide-functional linker designed for modular PROTAC and targeted protein degradation workflows. Structurally, it comprises a short polyethylene glycol chain terminated with an azide handle and capped with a tert-butyl acetate group, providing a chemically stable yet reactive intermediate for downstream conjugation. In PROTAC assembly, the azide enables bioorthogonal “click” coupling (typically via Cu(I)-catalyzed or strain-promoted azide–alkyne cycloaddition) to attach the linker to complementary alkyne-bearing ligands, allowing efficient construction of heterobifunctional degraders. The PEG segment contributes aqueous solubility and conformational flexibility, which can improve productive engagement between the target-binding and E3-ligase–recruiting moieties. This linker is valuable for researchers optimizing linker length, attachment chemistry, and overall degradation performance, particularly when rapid synthesis of ligand–linker conjugates is required for structure–activity relationship studies.

Azido-PEG4-t-butyl acetate

Structure of 864681-04-9

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Category
PROTAC Linker
Molecular Formula
C14H27N3O6
Molecular Weight
333.38
Appearance
Solid

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

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Purity
>98.0%
Solubility
10 mm in DMSO
Appearance
Solid
ShelfLife
0-4°C for short term (days to weeks), or -20°C for long term (months).
Storage
-20°C
Shipping
Room temperature, or blue ice upon request.
IUPACName
tert-butyl 2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]acetate
Synonyms
Tert-butyl 14-azido-3,6,9,12-tetraoxatetradecanoate; Azido-PEG4-CH2CO2-t-Bu
InChI Key
SIOLYQZSIFQODW-UHFFFAOYSA-N
InChI
InChI=1S/C14H27N3O6/c1-14(2,3)23-13(18)12-22-11-10-21-9-8-20-7-6-19-5-4-16-17-15/h4-12H2,1-3H3
SMILES
CC(C)(C)OC(=O)COCCOCCOCCOCCN=[N+]=[N-]

Azido-PEG4-t-butyl acetate is a PEG-based cleavable linker building block designed for PROTAC assembly, offering a flexible hydrophilic spacer and a bioorthogonal azide handle for modular conjugation. Its protected ester functionality supports controlled coupling strategies, while the tert-butyl acetate motif can be leveraged to tune stability and release behavior during synthesis. The subsequent sections describe the linker’s structural features and practical reactivity considerations for constructing targeted protein degraders.

Structure: The linker contains an azide functional group attached to a polyethylene glycol chain, providing conformational flexibility and enhanced solubility. A tert-butyl acetate ester introduces a protected carbonyl linkage, with stable C–O and C–N connectivity and an azide-bearing N–N bond system suitable for click-type conjugation.

Reactivity: The azide group is compatible with copper-catalyzed azide–alkyne cycloaddition or related azide-based bioorthogonal coupling approaches under conditions that preserve sensitive ligands. Ester functionality enables coupling via standard ester chemistry, and the tert-butyl acetate protection can be managed through controlled deprotection or transesterification strategies to expose reactive alcohol/acid intermediates. Solvent selection typically favors polar organic media to maintain PEG solubility while minimizing side reactions.

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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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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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