Benzyl-PEG6-t-butyl acetate

 CAS No.: 1807537-31-0  Cat No.: BP-500232 4.5  

Benzyl-PEG6-t-butyl acetate is a PEG-based linker building block featuring a benzyl group at one terminus and a tert-butyl acetate functionality at the other, connected through a six-unit polyethylene glycol chain that provides a flexible, hydrophilic spacer. The PEG segment helps tune the effective distance and conformational freedom between a ligand warhead and a recruited E3 ligase moiety, which is critical for productive ternary-complex formation in PROTACs. In PROTAC synthesis, this type of linker is used to spatially separate binding elements while improving solubility and reducing nonspecific hydrophobic interactions. The terminal groups serve as chemically addressable handles for coupling reactions, enabling researchers to integrate the linker into larger targeted degradation constructs. As a modular PEG linker, it is valuable for systematic structure–activity relationship studies aimed at optimizing degradation efficiency, selectivity, and physicochemical properties of PROTAC candidates.

Benzyl-PEG6-t-butyl acetate

Structure of 1807537-31-0

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Category
PROTAC Linker
Molecular Formula
C₂₃H₃₈O₈
Molecular Weight
442.54
Appearance
Liquid

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

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Liquid
Storage
Please store the product under the recommended conditions in the Certificate of Analysis.
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Room temperature in continental US; may vary elsewhere.
IUPACName
tert-butyl 2-[2-[2-[2-[2-(2-phenylmethoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]acetate
Synonyms
tert-Butyl 1-phenyl-2,5,8,11,14,17-hexaoxanonadecan-19-oate; Benzyl-PEG6-CH2COOtBu
Boiling Point
507.3±45.0 °C at 760 mmHg
Density
1.1±0.1 g/cm3
InChI Key
HTCCPCCHDIEUTN-UHFFFAOYSA-N
InChI
InChI=1S/C23H38O8/c1-23(2,3)31-22(24)20-30-18-16-28-14-12-26-10-9-25-11-13-27-15-17-29-19-21-7-5-4-6-8-21/h4-8H,9-20H2,1-3H3
SMILES
CC(C)(C)OC(=O)COCCOCCOCCOCCOCCOCC1=CC=CC=C1

Benzyl-PEG6-t-butyl acetate is a PEG-based PROTAC linker designed to provide conformational flexibility and improved solubility, helping to connect a ligand-recruiting warhead to an E3-recruiting element while maintaining productive geometries for ternary complex formation. Its ether-rich PEG segment can reduce non-specific aggregation and support aqueous handling in degradation workflows. The points below describe the linker’s structural features and practical considerations for assembling PROTAC constructs.

Structure: The molecule contains a PEG chain segment terminated with a benzyl group and a t-butyl acetate moiety. It features ether linkages along the polyethylene glycol backbone and an ester functional group, with a relatively flexible, polar scaffold that promotes hydration and dispersion in typical organic/aqueous mixtures.

Reactivity: For PROTAC synthesis, this linker is commonly used as a protected, functional handle that can be converted into coupling-ready intermediates under standard ester-activation or deprotection/cap-exchange strategies. Reaction planning typically follows established ester chemistry: controlled hydrolysis or transesterification to reveal reactive alcohol functionality, followed by amide/ester/ether bond formation with complementary ligand fragments. Mild bases or acid catalysts, compatible solvents, and careful moisture control are generally required to preserve sensitive ligand groups.

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