N-Boc-N-bis(PEG4-azide)

 CAS No.: 2055041-25-1  Cat No.: BP-501483  Purity: 98% 4.5  

N-Boc-N-bis(PEG4-azide) is a protected, bis-functional polyethylene glycol linker bearing terminal azide groups, designed for modular PROTAC assembly. Structurally, it consists of a Boc-protected nitrogen core conjugated to two PEG4 arms, each terminating in an azide handle, providing a flexible, hydrophilic spacer with two orthogonal sites for chemoselective coupling. In targeted protein degradation workflows, such bis-azide PEG linkers are valuable for connecting or tuning the spatial relationship between a ligand (e.g., a warhead that binds an E3 ligase) and a second ligand or reactive intermediate, thereby influencing productive ternary complex formation and overall degradation efficiency. The PEG architecture can improve solubility and reduce nonspecific interactions, while the azide termini enable bioorthogonal conjugation strategies such as strain-promoted or copper-catalyzed azide–alkyne cycloaddition to incorporate other PROTAC modules under mild conditions. This makes the reagent a practical building block for systematic linker optimization in targeted degradation research.

N-Boc-N-bis(PEG4-azide)

Structure of 2055041-25-1

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Category
PROTAC Linker
Molecular Formula
C₂₅H₄₉N₇O₁₀
Molecular Weight
607.70

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

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Purity
98%
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
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Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl N,N-bis[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethyl]carbamate
Synonyms
tert-butyl bis(14-azido-3,6,9,12-tetraoxatetradecyl)carbamate; tert-butyl N,N-bis(14-azido-3,6,9,12-tetraoxatetradecan-1-yl)carbamate; tert-butyl N,N-bis[2-[2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]ethoxy]ethyl]carbamate; 5,8,11,14-Tetraoxa-2-azahexadecanoic acid, 16-azido-2-(14-azido-3,6,9,12-tetraoxatetradec-1-yl)-, 1,1-dimethylethyl ester
InChI Key
RTTMSYUZSFHWJC-UHFFFAOYSA-N
InChI
InChI=1S/C25H49N7O10/c1-25(2,3)42-24(33)32(6-10-36-14-18-40-22-20-38-16-12-34-8-4-28-30-26)7-11-37-15-19-41-23-21-39-17-13-35-9-5-29-31-27/h4-23H2,1-3H3
SMILES
CC(C)(C)OC(=O)N(CCOCCOCCOCCOCCN=[N+]=[N-])CCOCCOCCOCCOCCN=[N+]=[N-]

N-Boc-N-bis(PEG4-azide) is a PEG-based, bis-azide linker reagent designed to enable modular construction of PROTACs through orthogonal azide chemistry. Its PEG-rich architecture supports favorable solubility and conformational flexibility, while the azide termini provide reliable handles for bioorthogonal conjugation to targeting and E3-ligase ligands. The Boc-protected nitrogen further supports controlled functionalization during synthesis. Detailed structural and reaction guidance is provided below.

Structure: The linker contains a Boc-protected nitrogen connected to two PEG4 chains terminating in azide groups. It features ether-rich PEG segments, stable carbon–nitrogen and carbon–oxygen linkages, and azide functional groups suitable for click-type coupling. Overall, it is expected to show high polarity and improved aqueous compatibility relative to purely hydrocarbon linkers.

Reactivity: Azide groups are well-suited for copper-catalyzed azide–alkyne cycloaddition or related azide click strategies to assemble PROTAC architectures. Typical approaches use Cu(I) generated in situ, with compatible ligands to modulate copper reactivity, and polar organic or mixed aqueous solvents to maintain solubility of PEG-based intermediates. Boc protection can be retained during azide coupling steps and removed under standard acid-mediated conditions when subsequent amide or amine formation is required.

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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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