2,5,8,11-Tetraoxatridecan-13-yl 4-methylbenzenesulfonate

 CAS No.: 62921-76-0  Cat No.: BP-501605  Purity: 95% 4.5  

2,5,8,11-Tetraoxatridecan-13-yl 4-methylbenzenesulfonate is a polyethylene glycol–like, ether-rich linker building block featuring a long, flexible polyether chain capped with a terminal 4-methylbenzenesulfonate leaving group. The extended ether scaffold provides conformational mobility and aqueous compatibility, which are advantageous for PROTAC linker design where the geometry between the target-binding ligand and the E3 ligase ligand must be tuned to enable productive ternary complex formation. The sulfonate ester functions as an activated handle for subsequent nucleophilic substitution or coupling, allowing researchers to connect this linker to compatible nucleophiles (for example, amines or other nucleophilic groups) to generate stable PROTAC intermediates. This reagent is valuable for constructing modular targeted protein degradation conjugates, supporting systematic variation of linker length and attachment chemistry to optimize degradation potency and selectivity in experimental screening workflows.

2,5,8,11-Tetraoxatridecan-13-yl 4-methylbenzenesulfonate

Structure of 62921-76-0

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PROTAC Linker
Molecular Formula
C16H26O7S
Molecular Weight
362.44

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

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Purity
95%
Solubility
Moderately soluble
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate
Synonyms
2,5,8,11-TETRAOXATRIDECAN-13-YL 4-METHYLBENZENESULFONATE; m-PEG5-Tos
InChI Key
CRLOMMYKVYXMLY-UHFFFAOYSA-N
InChI
InChI=1S/C16H26O7S/c1-15-3-5-16(6-4-15)24(17,18)23-14-13-22-12-11-21-10-9-20-8-7-19-2/h3-6H,7-14H2,1-2H3
SMILES
CC1=CC=C(C=C1)S(=O)(=O)OCCOCCOCCOCCOC

This PROTAC linker, 2,5,8,11-Tetraoxatridecan-13-yl 4-methylbenzenesulfonate, is designed to provide a flexible polyether spacer and a reactive sulfonate leaving group for efficient conjugation between targeting ligands and E3-binding modules. Its ether-rich backbone supports favorable solubility and conformational adaptability, helping maintain productive ternary complex formation. The detailed structural and synthetic considerations for linker installation are provided below.

Structure: The linker contains a polyether chain composed of repeating ether oxygen atoms, terminating in a sulfonate ester derived from a methyl-substituted benzenesulfonyl group. It features stable C–O and S–O connectivity, with an aryl sulfonate functionality that serves as a leaving group under nucleophilic substitution conditions.

Reactivity: The sulfonate ester is well suited for nucleophilic substitution reactions with alcohol, amine, or other nucleophiles commonly used to connect PROTAC components. Typical conjugation proceeds via an SN2-type displacement at the activated carbon, often using polar aprotic solvents and mild base or acid scavenging strategies to promote nucleophile formation and suppress side reactions. Reaction temperature and stoichiometry should be optimized to balance conversion and stability of sensitive functional groups.

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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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