Hexaethylene glycol di-p-toluenesulfonate
CAS No.: 42749-27-9
Cat No.: BP-500800
Purity: ≥95%
4.5 
Hexaethylene glycol di-p-toluenesulfonate is a bifunctional, PEG-based linker reagent featuring two terminal p-toluenesulfonate leaving groups separated by a six-unit ethylene glycol chain. The extended, flexible poly(ethylene glycol) segment provides conformational freedom and aqueous compatibility, while the tosylate termini enable efficient nucleophilic substitution with PROTAC-relevant nucleophiles (for example, amines, thiols, or alcohols) to install handles that connect a ligand-derived warhead to an E3-recruiting module. In PROTAC design, this linker architecture helps tune the effective distance and relative orientation between the two binding domains, which is critical for productive ternary complex formation and subsequent ubiquitination-driven degradation. As a practical PEG linker, it supports systematic structure–activity studies by allowing modular synthesis of conjugates with improved solubility and reduced steric constraints, facilitating robust experimental evaluation of targeted protein degradation strategies.
Structure of 42749-27-9
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Hexaethylene glycol di-p-toluenesulfonate, is designed to provide a flexible, hydrophilic spacer that can bridge two reactive partners in targeted protein degradation constructs. Its sulfonate leaving groups enable efficient bond formation under standard organic synthesis conditions, supporting modular PROTAC assembly and optimization of linker length, solubility, and spatial orientation. The following sections describe the structure and practical reactivity considerations in detail.
Structure: The linker consists of a hexaethylene glycol backbone terminated by two p-toluenesulfonate (tosylate) ester groups. It contains ether linkages that confer flexibility and water-compatible polarity, alongside sulfonate ester functionalities. These features promote conformational mobility while maintaining chemically addressable termini for subsequent coupling.
Reactivity: Tosylate esters are activated electrophiles suitable for nucleophilic substitution reactions. In PROTAC linker construction, they are typically employed to form new C–O or C–N bonds by reacting with appropriate nucleophiles such as alkoxides or amines. Common approaches use polar aprotic solvents and base-mediated activation to generate the nucleophile, with reaction conditions selected to favor substitution over side reactions. Careful control of stoichiometry and temperature supports clean coupling and reproducible linker installation.
* 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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