N-(Tos-PEG4)-N-bis(PEG4-Boc)

 CAS No.: 2112737-74-1  Cat No.: BP-501127 4.5  

N-(Tos-PEG4)-N-bis(PEG4-Boc) is a PEG-based PROTAC linker building block featuring one tosylate leaving group and two PEG4 arms terminated as tert-butyl ester-protected carboxylic acids. Structurally, the compound provides flexible, hydrophilic chain length that reduces steric constraints and helps position conjugated ligands at appropriate distances for productive ternary complex formation. In PROTAC design, such linkers serve as the “molecular bridge” that connects an E3 ligase–binding moiety to a target-binding ligand, enabling efficient proximity-driven recruitment of the ubiquitin–proteasome pathway. The tosyl group supports robust synthetic attachment to nucleophilic partners, while the tert-butyl esters can be removed to reveal carboxylic acids for stepwise functionalization during assembly. This reagent is valuable for constructing modular, water-soluble degraders and for optimizing linker length and reactivity in targeted protein degradation research.

N-(Tos-PEG4)-N-bis(PEG4-Boc)

Structure of 2112737-74-1

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PROTAC Linker
Molecular Formula
C₄₅H₈₁NO₁₈S
Molecular Weight
956.19

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

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IUPACName
tert-butyl 3-[2-[2-[2-[2-[2-[2-[2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethoxy]ethoxy]ethyl-[2-[2-[2-[2-[3-[(2-methylpropan-2-yl)oxy]-3-oxopropoxy]ethoxy]ethoxy]ethoxy]ethyl]amino]ethoxy]ethoxy]ethoxy]ethoxy]propanoate
InChI Key
QKOYKXTUNUZJPX-UHFFFAOYSA-N
InChI
InChI=1S/C45H81NO18S/c1-40-8-10-41(11-9-40)65(49,50)62-39-38-61-37-36-60-31-26-55-21-16-46(14-19-53-24-29-58-34-32-56-27-22-51-17-12-42(47)63-44(2,3)4)15-20-54-25-30-59-35-33-57-28-23-52-18-13-43(48)64-45(5,6)7/h8-11H,12-39H2,1-7H3
SMILES
CC1=CC=C(C=C1)S(=O)(=O)OCCOCCOCCOCCN(CCOCCOCCOCCOCCC(=O)OC(C)(C)C)CCOCCOCCOCCOCCC(=O)OC(C)(C)C

This PROTAC linker reagent, N-(Tos-PEG4)-N-bis(PEG4-Boc), is designed to provide a PEG-based, solubilizing spacer while incorporating orthogonally protected functional handles for stepwise conjugation. Its ether-rich backbone supports favorable aqueous compatibility and flexibility, which are commonly leveraged to tune degrader geometry and minimize nonproductive interactions. The subsequent sections describe its structural traits and practical reactivity considerations for constructing PROTACs.

Structure: The molecule contains a tosyl (tosylate) group and multiple PEG segments, connected through ether linkages, creating a flexible, hydrophilic scaffold. It also bears two tert-butyl ester-protected carboxyl functionalities, enabling controlled deprotection and subsequent coupling without disturbing other reactive sites.

Reactivity: The tosylate functionality is typically used as an electrophile for nucleophilic substitution with amines or other suitable nucleophiles under standard organic synthesis conditions. The tert-butyl esters are generally removed under acid-mediated conditions to reveal carboxylic acids for further amide-forming coupling. For PROTAC assembly, stepwise protection/deprotection and orthogonal coupling strategies are commonly employed to preserve linker integrity and achieve site-selective conjugation.

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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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