Azido-PEG6-t-butyl ester

 CAS No.: 406213-76-1  Cat No.: BP-500430  Purity: >97% 4.5  

Azido-PEG6-t-butyl ester is a polyethylene glycol linker bearing a terminal azide group and a protected carboxyl functionality as a tert-butyl ester. Structurally, it provides a flexible, hydrophilic six-unit PEG spacer that can extend and spatially separate PROTAC-relevant binding motifs, while the azide enables efficient bioorthogonal conjugation via copper-free or copper-catalyzed azide–alkyne cycloaddition to attach to alkyne-bearing ligands, handles, or reporter tags. The tert-butyl ester serves as a stable, masked carboxyl group during synthesis and purification, allowing subsequent deprotection to generate a free carboxyl for amide coupling or other linkage strategies commonly used to connect E3 ligands and target-binding warheads. In targeted protein degradation research, such PEG-azide linkers help tune linker length, reduce steric interference, and improve conjugate solubility, thereby supporting systematic optimization of PROTAC architecture and degradation performance.

Azido-PEG6-t-butyl ester

Structure of 406213-76-1

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Category
PROTAC Linker
Molecular Formula
C19H37N3O8
Molecular Weight
435.51
Appearance
Colorless Liquid

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

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Purity
>97%
Solubility
Soluble in DMSO
Appearance
Colorless 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-azidoethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
Synonyms
N3-PEG6-CH2CH2COOtBu; 2-Methyl-2-propanyl 1-azido-3,6,9,12,15,18-hexaoxahenicosan-21-oate; N3-PEG6-tBu; Azido-PEG6-C2-Boc; tert-butyl 1-azido-3,6,9,12,15,18-hexaoxahenicosan-21-oate; Azido-PEG6-Boc; 3,6,9,12,15,18-Hexaoxaheneicosan-21-oic acid, 1-azido-, 1,1-dimethylethyl ester; 21-Azido-4,7,10,13,16,19-hexaoxaheneicosanoic acid 1,1-dimethylethyl ester
InChI Key
HRNUWAOLFSWRDG-UHFFFAOYSA-N
InChI
InChI=1S/C19H37N3O8/c1-19(2,3)30-18(23)4-6-24-8-10-26-12-14-28-16-17-29-15-13-27-11-9-25-7-5-21-22-20/h4-17H2,1-3H3
SMILES
CC(C)(C)OC(=O)CCOCCOCCOCCOCCOCCOCCN=[N+]=[N-]

Azido-PEG6-t-butyl ester is a PEG-based, azide-functional linker designed for modular assembly of PROTACs, enabling efficient conjugation between targeting ligands and E3 ligase recruiters. Its ether-rich polyethylene glycol segment supports favorable solubility and conformational flexibility, while the azide handle provides a widely used bioorthogonal attachment site. The protected carboxyl functionality supports controlled coupling strategies during synthesis. Detailed structural and reactivity considerations are provided below.

Structure: This linker contains an azide group for orthogonal conjugation, a polyethylene glycol chain that provides hydrophilicity and flexibility, and a tert-butyl ester protecting group that masks the carboxylic acid during earlier steps. Its connectivity features ether linkages along the PEG backbone and ester carbonyl functionality.

Reactivity: The azide moiety is typically engaged via azide–alkyne cycloaddition under copper catalysis or via copper-free methods using strained alkynes, enabling attachment to alkyne-bearing partners. The tert-butyl ester can be deprotected under acid-promoted conditions to reveal a carboxylic acid for subsequent amide or ester-forming couplings. Common coupling approaches use carbodiimide-type reagents with appropriate bases in polar organic solvents.

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