1-Phenyl-2,5,8,11,14-pentaoxahexadecan-16-yl 4-methylbenzenesulfonate

 CAS No.: 129086-10-8  Cat No.: BP-501532  Purity: ≥95% 4.5  

1-Phenyl-2,5,8,11,14-pentaoxahexadecan-16-yl 4-methylbenzenesulfonate is a PEG-like, ether-rich linker bearing a terminal phenyl group and a sulfonate leaving group for controlled functionalization. Structurally, it consists of a long, flexible polyether chain with multiple oxygen atoms that enhance solubility and conformational freedom, while the terminal sulfonate activates the end of the linker toward nucleophilic substitution. In PROTAC design, such activated linkers are used to connect a ligand or warhead-bearing nucleophile to the complementary partner, enabling the formation of a stable conjugate that can span the distance between the target-binding moiety and the E3 ligase ligand. The ether-rich backbone can reduce steric penalties and help maintain productive ternary-complex formation by allowing relative reorientation of the two binding domains. This reagent is valuable for constructing modular targeted degradation probes, facilitating systematic linker-length and polarity optimization in experimental workflows.

1-Phenyl-2,5,8,11,14-pentaoxahexadecan-16-yl 4-methylbenzenesulfonate

Structure of 129086-10-8

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Category
PROTAC Linker
Molecular Formula
C24H34O8S
Molecular Weight
482.59
Appearance
Pale Yellow or Colorless Oily Matter

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

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Purity
≥95%
Appearance
Pale Yellow or Colorless Oily Matter
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
2-[2-[2-[2-(2-phenylmethoxyethoxy)ethoxy]ethoxy]ethoxy]ethyl 4-methylbenzenesulfonate
Synonyms
Benzyl-PEG5-Ots; Tosylate of Pentaethylene glycol monobenzyl ether; Bn-P5-OTs; TosO-(CH2CH2O)5-Bn; 2,5,8,11,14-Pentaoxahexadecan-16-ol, 1-phenyl-, 4-methylbenzenesulfonate
Boiling Point
587.0±50.0°C at 760 mmHg
Density
1.2±0.1 g/cm3
InChI Key
DKGINCKIMWNUHS-UHFFFAOYSA-N
InChI
InChI=1S/C24H34O8S/c1-22-7-9-24(10-8-22)33(25,26)32-20-19-30-16-15-28-12-11-27-13-14-29-17-18-31-21-23-5-3-2-4-6-23/h2-10H,11-21H2,1H3
SMILES
CC1=CC=C(C=C1)S(=O)(=O)OCCOCCOCCOCCOCCOCC2=CC=CC=C2

This PROTAC linker, 1-Phenyl-2,5,8,11,14-pentaoxahexadecan-16-yl 4-methylbenzenesulfonate, is designed to serve as a chemically robust coupling handle for assembling heterobifunctional degraders. Its ether-rich scaffold provides conformational flexibility and favorable solubility characteristics, while the sulfonate leaving group enables efficient bond formation under standard synthetic conditions. The following sections describe the linker’s structure and the practical reactivity considerations relevant to PROTAC construction.

Structure: The molecule contains a long, pentaoxaether chain incorporating multiple ether oxygen atoms, connected to a phenyl-bearing terminus. It features an aryl sulfonate ester at the reactive end, with aromatic rings and ether linkages that together support flexibility and polarity.

Reactivity: The sulfonate ester is suited for nucleophilic substitution reactions used to connect PROTAC warheads and ligands. In typical linker-assembly workflows, base-mediated activation of a nucleophile (such as an alcohol, thiol, or amine) promotes displacement of the sulfonate group via an SN-type mechanism under anhydrous, inert or controlled conditions. Common solvents include polar aprotic media, and catalysts are selected based on nucleophile identity and compatibility with 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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