Tos-PEG3-alcohol

 CAS No.: 77544-68-4  Cat No.: BP-500031 4.5  

Tos-PEG3-alcohol is a tosyl-terminated polyethylene glycol linker bearing a terminal hydroxyl group, providing a short, flexible PEG spacer between a sulfonate leaving group and an alcohol handle. Structurally, it consists of a tosyl (p-toluenesulfonyl) moiety attached to a PEG chain of three ethylene glycol units, with the opposite end functionalized for subsequent conjugation. In PROTAC and targeted protein degradation workflows, this linker is commonly used as a modular intermediate to install PEG spacers that tune solubility, reduce steric congestion, and control the effective distance and orientation between the ligand-binding domain and the recruiter/warhead. The tosyl group can serve as an activated electrophile for nucleophilic substitution, enabling efficient attachment to amine or other nucleophiles, while the terminal alcohol permits further derivatization (e.g., to reactive carbonate/ester or ether derivatives). Its value lies in facilitating systematic linker optimization to improve degradation potency and selectivity in structure–activity studies.

Tos-PEG3-alcohol

Structure of 77544-68-4

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Category
PROTAC Linker
Molecular Formula
C₁₃H₂₀O₆S
Molecular Weight
304.36
Appearance
Liquid

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

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Solubility
In Ethanol: 100 mg/mL (328.56 mM; Need ultrasonic)<br/>In DMSO: 100 mg/mL (328.56 mM; Need ultrasonic and warming)<br/>In H2O: 10 mg/mL (32.86 mM; Need ultrasonic)
Appearance
Liquid
Storage
Pure form, -20°C, 3 years; 4°C, 2 years; In solvent, -80°C, 6 months; -20°C, 1 month
Shipping
Room temperature in continental US; may vary elsewhere.
IUPACName
2-[2-(2-hydroxyethoxy)ethoxy]ethyl 4-methylbenzenesulfonate
Synonyms
PEG3-Tos; 2-(2-(2-Hydroxyethoxy)ethoxy)ethyl 4-methylbenzenesulfonate
Boiling Point
460.0±35.0 °C at 760 mmHg
Density
1.2±0.1 g/cm3
InChI Key
RSUCRUOTLCQWFX-UHFFFAOYSA-N
InChI
InChI=1S/C13H20O6S/c1-12-2-4-13(5-3-12)20(15,16)19-11-10-18-9-8-17-7-6-14/h2-5,14H,6-11H2,1H3
SMILES
CC1=CC=C(C=C1)S(=O)(=O)OCCOCCOCCO
ConcentrationVolumeMass1 mg5 mg10 mg
1 mM3.2856 mL16.4279 mL32.8558 mL
5 mM0.6571 mL3.2856 mL6.5712 mL
10 mM0.3286 mL1.6428 mL3.2856 mL

Tos-PEG3-alcohol is a PEG-based linker reagent designed for modular construction of PROTACs, enabling efficient conjugation between a ligand and an E3-recruiting module while improving solubility and reducing steric constraints. Its ether-rich architecture supports flexible linker conformations that can enhance productive ternary complex formation. The points below describe the structure and practical reactivity considerations for PROTAC synthesis and characterization.

Structure: The linker comprises a tosyl-activated PEG chain terminated with an alcohol, featuring an aromatic tosyl group and multiple ether linkages along the polyethylene glycol backbone. The molecule contains sulfonate-derived leaving group functionality and a primary alcohol handle, providing a versatile platform for subsequent bond formation.

Reactivity: The tosyl group enables nucleophilic substitution reactions where the alcohol-containing PEG segment can be transformed into coupling-ready intermediates. PROTAC assembly commonly proceeds via substitution or derivatization steps that link ligands through stable ether or related linkages. Typical conditions use polar aprotic solvents and base-promoted nucleophile generation; reaction rates depend on nucleophile strength and substrate accessibility, and purification is generally required to remove sulfonate byproducts.

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It is commonly abbreviated as: C1V1 = C2V2

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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