Tetraethylene glycol dimethanesulfonate
CAS No.: 55400-73-2
Cat No.: BP-500805
Purity: 95%
4.5 
Tetraethylene glycol dimethanesulfonate is a bifunctional linker derived from tetraethylene glycol in which both termini are converted to methanesulfonate leaving groups. Structurally, it provides a flexible, hydrophilic chain length consistent with PEG-like spacers, while the terminal sulfonate esters enable efficient nucleophilic substitution. In PROTAC design, this type of linker is used to connect two functional fragments—typically an amine, alcohol, or other nucleophile-bearing handles on a ligand or warhead—through sequential alkylation at the sulfonate termini, yielding stable ether or related linkage architectures depending on the nucleophile employed. The flexible polyether backbone helps maintain productive relative orientation and reduces steric constraints between the recruiting ligand and the target-binding moiety, which can improve formation of the ternary complex and thereby influence degradation potency. As a practical, reactive PEG-based linker, it supports modular synthesis and rapid optimization of targeted protein degradation constructs.
Structure of 55400-73-2
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This tetraethylene glycol dimethanesulfonate is a bifunctional PROTAC linker building block designed to connect ligand-bearing warheads through ether-rich spacing and activated methanesulfonate leaving groups. Its flexible polyether backbone can help tune effective molarity and reduce steric constraints in ternary-complex formation, while the sulfonate esters enable efficient nucleophilic substitution during linker assembly. The points below describe its structure-related features and practical reactivity considerations for PROTAC synthesis.
Structure: The linker comprises a tetraethylene glycol core bearing two terminal methanesulfonate ester groups, providing a flexible ether-rich scaffold. It contains sulfonate ester linkages with sulfonyl–oxygen bonds and multiple ether oxygen atoms that support polarity and hydrogen-bonding interactions. Overall, it behaves as a bifunctional electrophile under substitution conditions.
Reactivity: Methanesulfonate esters are well-suited for nucleophilic substitution with amines or other nucleophiles commonly used to install ligand handles in PROTACs. Linker coupling is typically performed under base-promoted conditions in polar aprotic solvents, where the nucleophile displaces the methanesulfonate leaving group via an SN2-type pathway. Careful control of temperature and stoichiometry helps minimize side reactions such as hydrolysis; inert atmosphere and anhydrous handling are often beneficial for reproducible linker formation.
* 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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