2-(2-(Benzyloxy)ethoxy)ethyl 4-methylbenzenesulfonate
CAS No.: 98627-22-6
Cat No.: BP-500313
Purity: ≥95%
4.5 
2-(2-(Benzyloxy)ethoxy)ethyl 4-methylbenzenesulfonate is a sulfonate ester linker featuring a benzyl-protected ethoxyethyl alcohol segment connected through an O-alkyl chain to a tosyl (4-methylbenzenesulfonyl) leaving group. Structurally, it combines an ether-containing hydrophilic spacer with a tosylate moiety that can be used to generate an activated electrophile for subsequent nucleophilic substitution. In PROTAC construction, such sulfonate linkers are commonly employed to install or exchange functional handles on one component (e.g., an alcohol-bearing ligand or intermediate), enabling controlled conjugation to a second module such as an E3 ligase binder or a targeting scaffold. The benzyl ether can provide temporary protection during multi-step synthesis, improving chemoselectivity, and can be removed under standard hydrogenolysis conditions to reveal the corresponding alcohol for further coupling. This makes the linker valuable for modular, stepwise assembly of targeted protein degradation probes where reliable functional-group interconversion is required.
Structure of 98627-22-6
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2-(2-(Benzyloxy)ethoxy)ethyl 4-methylbenzenesulfonate, provides a practical sulfonate handle for assembling bifunctional degraders. Its ether-rich architecture supports conformational flexibility and efficient spacing between targeting and recruitment modules. The benzyloxy-protected ethoxy motif can be advantageous during multi-step synthesis, enabling controlled functional group manipulation. The sections below describe its structure and the most commonly used reaction strategies for PROTAC construction.
Structure: The molecule is built around an alkyl sulfonate ester linked to an ethoxy-extended backbone. Multiple ether linkages and a benzyloxy substituent contribute to polarity and conformational flexibility. Aromatic sulfonate functionality provides a stable leaving group for nucleophilic substitution under appropriate conditions.
Reactivity: As a sulfonate ester, it is suited to nucleophilic substitution reactions to install the linker onto PROTAC-building fragments such as alcohol or amine-containing ligands. Typical conditions use polar aprotic solvents and base systems to generate the nucleophile, while preserving other protecting groups. The reaction proceeds via sulfonate-activated displacement, and subsequent deprotection steps may be employed when benzyl ethers require removal under hydrogenolysis or related protocols.
* 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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