t-Boc-N-Amido-PEG3-Amine

 CAS No.: 101187-40-0  Cat No.: BP-500002  Purity: >98% 4.5  

t-Boc-N-Amido-PEG3-Amine is a protected, bifunctional polyethylene glycol linker featuring a terminal primary amine for conjugation and an N-amide connection that supports stable attachment to PROTAC components. The structure incorporates a short PEG segment that provides hydrophilicity and conformational flexibility, while the t-Boc group serves as a removable protecting group to enable stepwise synthesis and controlled coupling. In PROTAC design, PEG-based linkers are widely used to tune the effective distance and relative orientation between the ligand that recruits an E3 ligase and the ligand that binds the target protein, thereby improving ternary-complex formation and degradation efficiency. This linker is particularly useful for assembling modular PROTACs where orthogonal functional groups are required for sequential functionalization, and where minimizing steric constraints can enhance productive engagement of both binding moieties.

t-Boc-N-Amido-PEG3-Amine

Structure of 101187-40-0

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Category
PROTAC Linker
Molecular Formula
C13H28N2O5
Molecular Weight
292.37
Related CAS
890091-42-6 (polymer) 198227-38-2 (polymer)
Appearance
Pale Yellow Oily Liquid

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

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Purity
>98%
Solubility
Soluble in DCM, DMF, DMSO, Water
Appearance
Pale Yellow Oily Liquid
Storage
Store at 2-8°C under inert gas (nitrogen or Argon)
Shipping
Room temperature in continental US; may vary elsewhere
IUPACName
tert-butyl N-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethyl]carbamate
Synonyms
NHBoc-PEG3-amine; 5,8,11-Trioxa-2-azatridecanoic, 13-amino-, 1,1-dimethylethyl ester; BOC-NH-PEG3-NH2; tert-Butyl (2-(2-(2-(2-aminoethoxy)ethoxy)ethoxy)ethyl)carbamate; N-Boc-1,11-diamino-3,6,9-trioxaundecane; tert-Boc-N-amido-PEG3-amine; Boc-N-Amido-PEG3-Amine; N-Boc-2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethanamine; 1-Boc-amino-11-bromo-3,6,9-trioxadecane; Carbamic acid, N-[2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethyl]-, 1,1-dimethylethyl ester; 2-Methyl-2-propanyl (2-{2-[2-(2-aminoethoxy)ethoxy]ethoxy}ethyl)carbamate
Boiling Point
405.7±35.0 °C at 760 mmHg
Density
1.05 g/cm<sup>3</sup>
InChI Key
CUPBLDPRUBNAIE-UHFFFAOYSA-N
InChI
InChI=1S/C13H28N2O5/c1-13(2,3)20-12(16)15-5-7-18-9-11-19-10-8-17-6-4-14/h4-11,14H2,1-3H3,(H,15,16)
SMILES
CC(C)(C)OC(=O)NCCOCCOCCOCCN

t-Boc-N-Amido-PEG3-Amine, is designed to provide a flexible polyethylene glycol spacer with an amine handle for controlled conjugation. Its amide-bearing connectivity and protected amine enable stepwise assembly of bifunctional degraders, supporting reliable linker installation and minimizing undesired side reactions. The subsequent sections describe the structural features and practical reactivity considerations for constructing PROTACs using this linker.

Structure: The molecule contains a Boc-protected amine, a PEG-based ethylene glycol segment, and an amide linkage that together confer conformational flexibility and improved solubility. It features stable covalent C–N and C–O bonds, with a carbamate (Boc) protecting group and an amide carbonyl providing defined hydrogen-bonding characteristics.

Reactivity: The Boc group can be removed under standard acid-mediated deprotection conditions to reveal the primary amine for coupling. PROTAC assembly commonly employs amine-reactive electrophiles (e.g., activated esters, isocyanates, or sulfonyl derivatives) to form stable amide or related linkages. Typical workflows use polar aprotic solvents, base-assisted activation where appropriate, and temperature control to preserve sensitive functional groups on targeting ligands.

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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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