Hydroxy-PEG6-t-butyl acetate

 CAS No.: 297162-47-1  Cat No.: BP-501123  Purity: >95% 4.5  

Hydroxy-PEG6-t-butyl acetate is a PEG-based linker bearing a terminal hydroxyl group and a protected tert-butyl acetate functionality, providing a chemically versatile, water-compatible scaffold for PROTAC construction. The PEG6 segment supplies a flexible, hydrophilic spacer that can reduce steric interference between the two binding modules of a PROTAC, helping maintain productive geometries for ternary complex formation. The terminal hydroxyl enables straightforward conjugation strategies (for example, ester or ether formation after appropriate activation), allowing attachment to ligands or reactive handles while preserving solubility in aqueous assay buffers. In PROTAC design, such linkers are used to tune effective distance and conformational freedom between the E3 ligase recruiter and the target-binding moiety, which can directly influence degradation potency and selectivity in cellular experiments. This product is therefore valuable for systematic linker optimization, facilitating reproducible synthesis of degraders and enabling comparative studies of how linker length, polarity, and functional group chemistry impact targeted protein degradation outcomes.

Hydroxy-PEG6-t-butyl acetate

Structure of 297162-47-1

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Category
PROTAC Linker
Molecular Formula
C₁₈H₃₆O₉
Molecular Weight
396.47
Appearance
Transparent Liquid

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

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Purity
>95%
Appearance
Transparent 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
tert-butyl 2-[2-[2-[2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]acetate
Synonyms
Hydroxy-PEG6-CH2COOtBu; HO-PEG6-CH2COOtBu; tert-Butyl 20-hydroxy-3,6,9,12,15,18-hexaoxaicosanoate
Boiling Point
469.5±40.0 °C at 760 mmHg
Density
1.1±0.1 g/cm3
InChI Key
BHPCFQUBUVPQGG-UHFFFAOYSA-N
InChI
InChI=1S/C18H36O9/c1-18(2,3)27-17(20)16-26-15-14-25-13-12-24-11-10-23-9-8-22-7-6-21-5-4-19/h19H,4-16H2,1-3H3
SMILES
CC(C)(C)OC(=O)COCCOCCOCCOCCOCCOCCO

Hydroxy-PEG6-t-butyl acetate is a polyethylene glycol-based linker designed for modular synthesis of PROTACs, offering improved solubility, conformational flexibility, and reduced nonspecific interactions through its PEG segment. The terminal hydroxy handle supports controlled conjugation to ligands, while the tert-butyl ester-protected carboxyl group enables strategic functional group interconversion during assembly. These features facilitate efficient construction of targeted degradation molecules; the following points describe its structure and practical reactivity considerations in detail below.

Structure: The linker comprises a PEG chain bearing a free hydroxy functionality and a tert-butyl ester protecting a carboxylic acid. It contains ether linkages within the PEG backbone and an ester linkage at the protected terminus, yielding a polar, flexible scaffold suitable for solvation and linker tuning.

Reactivity: For PROTAC assembly, the hydroxy group is typically used for nucleophilic substitution, esterification, or coupling to activated ligand fragments under standard organic synthesis conditions. The tert-butyl ester can be removed by mild acid to reveal the carboxylic acid; the alcohol is already present as a free hydroxy group. Common approaches employ alcohol activation reagents and coupling chemistries in polar aprotic solvents, with careful control of acidity to preserve other sensitive groups.

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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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