t-boc-N-amido-PEG3-alcohol

 CAS No.: 139115-92-7  Cat No.: BP-500008  Purity: >95% 4.5  

t-Boc-N-amido-PEG3-alcohol is a PEG-based linker building block featuring a Boc-protected amide functionality and a short, three-unit poly(ethylene glycol) chain terminating in a primary alcohol. Structurally, the PEG segment provides conformational flexibility and aqueous solubility, while the amide handle enables controlled conjugation chemistry through standard coupling or derivatization strategies. In PROTAC and targeted protein degradation designs, this linker is used to spatially separate the ligand-binding warhead from the recruiting or E3-binding module, tuning effective ternary-complex formation by modulating linker length, polarity, and local dynamics. The terminal alcohol can be converted into activated derivatives (e.g., esters or ethers) to facilitate attachment to carboxylate- or hydroxyl-bearing partners, supporting stepwise assembly of degraders. This compound is valuable for researchers seeking reliable, modular PEG linkers to optimize degradation potency and selectivity while maintaining synthetic tractability and compatibility with iterative PROTAC synthesis workflows.

t-boc-N-amido-PEG3-alcohol

Structure of 139115-92-7

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Category
PROTAC Linker
Molecular Formula
C11H23NO5
Molecular Weight
249.30
Related CAS
159156-95-3 (polymer)
Appearance
Light Yellow Oily Liquid

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

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Purity
>95%
Solubility
Soluble in Chloroform (Slightly), Methanol (Slightly)
Appearance
Light Yellow Oily Liquid
Storage
Store at 2-8°C
Shipping
Room temperature in continental US; may vary elsewhere
IUPACName
tert-butyl N-[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]carbamate
Synonyms
NHBoc-PEG3-OH; 2-[2-(2-t-Boc-aminoethoxy]ethoxy]ethanol; N-[2-[2-(2-Hydroxyethoxy)ethoxy]ethyl]carbamic Acid 1,1-Dimethylethyl Ester; 2-[2-(2-tert-Butyloxycarbonylaminoethoxy)ethoxy]ethanol; Boc-NH-PEG3; Carbamic acid, N-[2-[2-(2-hydroxyethoxy)ethoxy]ethyl]-, 1,1-dimethylethyl ester; 2-Methyl-2-propanyl {2-[2-(2-hydroxyethoxy)ethoxy]ethyl}carbamate; Boc-NH-PEG3-OH; N-Boc-PEG3-alcohol
Boiling Point
374.6±27.0°C (Predicted)
Density
1.071±0.06 g/cm3 (Predicted)
InChI Key
FMLOTGGIHAYZLW-UHFFFAOYSA-N
InChI
InChI=1S/C11H23NO5/c1-11(2,3)17-10(14)12-4-6-15-8-9-16-7-5-13/h13H,4-9H2,1-3H3,(H,12,14)
SMILES
CC(C)(C)OC(=O)NCCOCCOCCO

t-boc-N-amido-PEG3-alcohol, is a PEG-based, functionalized alcohol designed to serve as a flexible spacer for assembling bifunctional degraders. Its ether-rich backbone provides conformational mobility and improved solubility, while the protected amide functionality enables controlled coupling to targeting ligands and E3-recruiting warheads. The alcohol handle supports site-selective derivatization, making it well suited for linker engineering in targeted protein degradation workflows. The following points describe its structural and synthetic reactivity in detail below.

Structure: The molecule contains a short polyethylene glycol segment featuring ether linkages, terminating in an alcohol group for further functionalization. An amide motif is present and protected as a Boc carbamate, providing stability under many coupling conditions while enabling deprotection when required. The combination yields a flexible, polar linker.

Reactivity: The terminal alcohol can be activated for nucleophilic substitution or ester formation, enabling attachment to complementary PROTAC fragments under standard organic coupling strategies. The Boc-protected amide allows orthogonal synthesis: Boc can be removed using acid-mediated deprotection to reveal an amine for amide bond formation or urea/carbamate-type coupling. Typical approaches employ coupling reagents and polar aprotic solvents, with reaction conditions selected to preserve the PEG ether backbone and avoid side reactions.

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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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