Tos-PEG6-CH2-Boc

 CAS No.: 1530777-90-2  Cat No.: BP-501584 4.5  

Tos-PEG6-CH2-Boc is a heterobifunctional PEG-based linker bearing a tosyl (p-toluenesulfonyl) activated leaving group at one end and a methylene-linked tert-butyl ester-protected carboxyl functionality at the other, providing a flexible, water-soluble chain of intermediate length for PROTAC assembly. The tosyl group is designed to enable nucleophilic substitution by thiols or amines from complementary warhead or ligand fragments, allowing efficient formation of a stable covalent connection while maintaining the conformational mobility afforded by the PEG segment. In targeted protein degradation workflows, this linker helps position the two binding moieties (e.g., an E3 ligase binder and a target-binding ligand) at an appropriate spatial distance and orientation to promote productive ternary complex formation. Its PEG architecture also commonly improves aqueous handling and reduces nonspecific aggregation, supporting reproducible synthesis and downstream biochemical evaluation.

Tos-PEG6-CH2-Boc

Structure of 1530777-90-2

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Category
PROTAC Linker
Molecular Formula
C₂₅H₄₂O₁₁S
Molecular Weight
550.66

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

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Storage
Pure form, -20°C, 3 years; 4°C, 2 years; In solvent, -80°C, 6 months; -20°C, 1 month
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl 2-[2-[2-[2-[2-[2-[2-(4-methylphenyl)sulfonyloxyethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetate
InChI Key
OIPLDSHYHFUPLX-UHFFFAOYSA-N
InChI
InChI=1S/C25H42O11S/c1-22-5-7-23(8-6-22)37(27,28)35-20-19-33-16-15-31-12-11-29-9-10-30-13-14-32-17-18-34-21-24(26)36-25(2,3)4/h5-8H,9-21H2,1-4H3
SMILES
CC1=CC=C(C=C1)S(=O)(=O)OCCOCCOCCOCCOCCOCCOCC(=O)OC(C)(C)C

Tos-PEG6-CH2-Boc is a bifunctional PEG-based linker designed for modular assembly of PROTACs, enabling efficient connection between a targeting ligand and an E3-recruiting moiety. Its ether-rich PEG segment provides conformational flexibility and improved solubility, while the tert-butyl ester-protected carboxyl functionality supports controlled conjugation strategies. The sulfonate-derived leaving group and the tert-butyl ester-protected carboxyl handle facilitate stepwise synthesis under standard organic conditions. Detailed structural and reactivity considerations are provided below.

Structure: The linker comprises a PEG chain terminated with a sulfonate-type group and a methylene spacer, along with a tert-butyl ester-protected carboxyl group. It contains multiple ether linkages, which confer flexibility and polarity, and ester and sulfonate functionalities that influence stability under controlled deprotection conditions.

Reactivity: Tosyl-activated sulfonates are commonly employed for nucleophilic substitution with amines or other nucleophiles to form the PROTAC coupling bond. The tert-butyl ester can be carried through compatible synthesis steps and later cleaved using acid-mediated conditions to reveal the carboxylic acid for subsequent activation and coupling. Solvent systems are selected to balance solubility of PEG intermediates and nucleophiles, often using polar organic solvents under inert or controlled atmospheres as needed.

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* Our calculator is based on the following equation:
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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