Boc-PEG8-Boc

 CAS No.: 1432970-18-7  Cat No.: BP-500994 4.5  

Boc-PEG8-Boc is a homobifunctional polyethylene glycol linker bearing Boc-protected carboxylate groups at both termini, connected through an extended octaethylene glycol spacer. This symmetric architecture provides a versatile building block for PROTAC construction, where both Boc groups can be removed under standard acidic conditions, either simultaneously or sequentially, to reveal two free carboxylic acids for amide coupling with primary amine-containing ligands. The extended PEG chain confers substantial aqueous solubility and high conformational flexibility, both critical for accommodating the large intermolecular distances required for productive ternary complex formation between certain target proteins and E3 ubiquitin ligases. In PROTAC design, linker length is a critical determinant of degradation efficiency, and this compound represents the longer end of the homologous bis-Boc PEG series, enabling researchers to explore the conformational space accessible with extended, high-flexibility linkers. The symmetric, bis-protected design simplifies synthetic workflows and enables the construction of symmetric or asymmetric PROTAC architectures through sequential deprotection and coupling. Researchers utilize this linker to systematically investigate how extended PEG spacer lengths influence degradation potency, selectivity, and physicochemical properties in targeted protein degradation research.

Boc-PEG8-Boc

Structure of 1432970-18-7

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PROTAC Linker
Molecular Formula
C₂₈H₅₄O₁₃
Molecular Weight
598.72

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

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Please store the product under the recommended conditions in the Certificate of Analysis.
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IUPACName
tert-butyl 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetate
InChI Key
QKDKAEGBTCSQLG-UHFFFAOYSA-N
InChI
InChI=1S/C28H54O13/c1-27(2,3)40-25(29)23-38-21-19-36-17-15-34-13-11-32-9-7-31-8-10-33-12-14-35-16-18-37-20-22-39-24-26(30)41-28(4,5)6/h7-24H2,1-6H3
SMILES
CC(C)(C)OC(=O)COCCOCCOCCOCCOCCOCCOCCOCCOCC(=O)OC(C)(C)C

This symmetric, extended oligoether linker is a protected dicarboxylic spacer for joining amine-functionalized PROTAC components. Its ether-rich chain offers substantial conformational freedom, while acid-labile termini enable conversion to a bifunctional coupling scaffold. Structural and reaction characteristics are described below.

Structure: An extended oligoether chain is bounded by equivalent tert-butyl acetate groups. The molecule contains many flexible ether bonds, terminal ester carbonyls, and no free nucleophile or acid. Its symmetry gives comparable intrinsic reactivity at both protected carboxyl termini.

Reactivity: Acidic treatment converts the terminal tert-butyl esters into carboxylic acids. Activation with a carbodiimide, phosphonium, or uronium reagent enables amide formation with amine-bearing ligands in a dry polar aprotic solvent and a suitable base. To prepare an unsymmetrical PROTAC, control stoichiometry or isolate a monoacylated intermediate before coupling the remaining acid, thereby limiting symmetric products and oligomerization.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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