t-boc-N-amido-PEG5-alcohol

 CAS No.: 1404111-67-6  Cat No.: BP-500905  Purity: >95% 4.5  

t-Boc-N-amido-PEG5-alcohol is a polyethylene glycol–based linker bearing a terminal primary alcohol and a protected amide functionality, where the t-Boc group provides orthogonal stability for subsequent coupling steps. Structurally, it combines a flexible PEG chain of intermediate length with an N-amide handle, enabling controlled conjugation to PROTAC warheads and E3 ligase ligands while maintaining solubility and reducing nonspecific hydrophobic interactions. In PROTAC architectures, such PEG linkers act as molecular “spacers” that tune the effective distance and relative orientation between binding moieties, often improving productive ternary complex formation and thereby supporting targeted protein degradation workflows. The terminal alcohol can be converted to activated derivatives (e.g., esters or ethers) for further functionalization, while the amide provides a robust attachment point for peptide or small-molecule conjugation strategies. This product is valuable for systematic linker optimization in degraders, facilitating reproducible synthesis of analog series for structure–activity relationship studies.

t-boc-N-amido-PEG5-alcohol

Structure of 1404111-67-6

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Category
PROTAC Linker
Molecular Formula
C15H31NO7
Molecular Weight
337.41
Related CAS
159156-95-3 (polymer)
Appearance
Pale Yellow Oily Liquid

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

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Purity
>95%
Solubility
Soluble in DCM, Methanol
Appearance
Pale 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-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethyl]carbamate
Synonyms
NHBoc-PEG5-OH; N-Boc-PEG5-alcohol; tert-Butyl (14-hydroxy-3,6,9,12-tetraoxatetradecyl)carbamate; Boc-NH-PEG5-OH; 5,8,11,14-Tetraoxa-2-azahexadecanoic acid, 16-hydroxy-, 1,1-dimethylethyl ester; 2-Methyl-2-propanyl (14-hydroxy-3,6,9,12-tetraoxatetradec-1-yl)carbamate; Carbamic acid, N-(14-hydroxy-3,6,9,12-tetraoxatetradec-1-yl)-, 1,1-dimethylethyl ester
Boiling Point
451.5±40.0°C (Predicted)
Density
1.083±0.06 g/cm3 (Predicted)
InChI Key
PBWLVPPLXJCLBC-UHFFFAOYSA-N
InChI
InChI=1S/C15H31NO7/c1-15(2,3)23-14(18)16-4-6-19-8-10-21-12-13-22-11-9-20-7-5-17/h17H,4-13H2,1-3H3,(H,16,18)
SMILES
CC(C)(C)OC(=O)NCCOCCOCCOCCOCCO

This linker reagent, t-boc-N-amido-PEG5-alcohol, is designed to provide a poly(ethylene glycol)-based spacer with an N-amide handle and a protected amine functionality, supporting robust conjugation strategies in PROTAC assembly. Its ether-rich, flexible architecture can enhance solubility and reduce steric constraints between binding ligands, while the protected group enables controlled stepwise coupling. Detailed structural and reactivity considerations are provided below.

Structure: The molecule features a PEG-derived ether chain that offers conformational flexibility, coupled to an N-amide linkage and a terminal alcohol. A Boc-protected nitrogen provides a stable, masked amine. The presence of multiple heteroatoms supports hydrogen bonding and improved aqueous compatibility.

Reactivity: The terminal alcohol and the amide/activated nitrogen functionality enable common PROTAC linker attachment workflows, including esterification or ether-forming coupling after appropriate activation. The Boc group is typically removed under mild acid conditions to reveal the amine for subsequent amide bond formation. Standard peptide-coupling chemistries and compatible polar solvents are generally used for stepwise conjugation, following established PROTAC linker synthesis principles.

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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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