Benzyl-PEG3-CH2-Boc

 CAS No.: 1443467-88-6  Cat No.: BP-500278 4.5  

Benzyl-PEG3-CH2-Boc is a doubly protected PEG linker precursor. Structurally, it contains a benzyl-protected hydroxyl terminus, a PEG3 chain, and an acetic acid terminus protected as a tert-butyl ester. Hydrogenolysis removes the benzyl ether to reveal an alcohol, whereas acid treatment cleaves the tert-butyl ester to give a carboxylic acid; either group can then be converted into a suitable coupling handle. In PROTAC and related targeted protein degradation research, the different protecting groups enable sequential exposure of alcohol and acid functionalities during modular linker synthesis. Its defined architecture allows researchers to evaluate how linker polarity, flexibility, attachment sequence, and terminal-group selection influence conjugate preparation and the spatial requirements of productive target–E3 ligase engagement. Clear assignment of the protected and reactive groups also supports reproducible reaction planning and systematic comparison of alternative linker designs in research-focused targeted protein degradation workflows.

Benzyl-PEG3-CH2-Boc

Structure of 1443467-88-6

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PROTAC Linker
Molecular Formula
C₁₉H₃₀O₆
Molecular Weight
354.44

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

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IUPACName
tert-butyl 2-[2-[2-(2-phenylmethoxyethoxy)ethoxy]ethoxy]acetate
InChI Key
CPMNHAPGRNEYDX-UHFFFAOYSA-N
InChI
InChI=1S/C19H30O6/c1-19(2,3)25-18(20)16-24-14-12-22-10-9-21-11-13-23-15-17-7-5-4-6-8-17/h4-8H,9-16H2,1-3H3
SMILES
CC(C)(C)OC(=O)COCCOCCOCCOCC1=CC=CC=C1

Benzyl-PEG3-CH2-Boc is a PEG-based PROTAC linker building block designed to provide a flexible, solubilizing tether between a ligand and an electrophilic handle for controlled conjugation. Its ether-rich chain supports conformational adaptability and can help tune effective distance and orientation in ternary-complex formation. The Boc-protected functionality enables stepwise synthesis, allowing researchers to assemble PROTACs with improved synthetic control. The structure and reactivity considerations are described in detail below.

Structure: The linker contains a benzyl group attached to a short poly(ethylene glycol) segment and a methylene spacer, providing ether-linked flexibility. A Boc-protected functional group offers a stable carbamate motif under mild conditions. Overall, the PEG character imparts enhanced polarity and solubility relative to purely hydrocarbon tethers.

Reactivity: Boc-protected linkers are typically used in stepwise PROTAC synthesis, where the Boc group can be removed under standard acid-mediated deprotection conditions to reveal a reactive amine or related nucleophile for subsequent coupling. Conjugation to ligands is commonly achieved via carbamate/amide-forming reactions using activated carboxylic acids, activated esters, or coupling reagents in compatible solvents. The PEG chain generally remains stable under these transformations, supporting reliable assembly workflows.

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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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