t-boc-N-amido-PEG8-alcohol

 CAS No.: 1345337-22-5  Cat No.: BP-500538  Purity: >97% 4.5  

t-boc-N-amido-PEG8-alcohol is a heterobifunctional PEG linker with an N-protected amine and an alcohol. Structurally, it contains an N-Boc-protected primary amine connected through PEG8 to a terminal hydroxyl group. The alcohol can be activated, esterified, etherified, or converted into a leaving group, while acid-mediated N-Boc removal reveals a primary amine for amide, urea, carbamate, or sulfonamide formation. In PROTAC and related targeted protein degradation research, the differentiated alcohol and protected amine support sequential functionalization across a long hydrophilic spacer and should not be described as a Boc-protected amide. Its defined architecture allows researchers to evaluate how linker polarity, flexibility, attachment sequence, and terminal-group selection influence conjugate preparation and the spatial requirements of productive target–E3 ligase engagement. Clear assignment of the protected and reactive groups also supports reproducible reaction planning and systematic comparison of alternative linker designs in research-focused targeted protein degradation workflows.

t-boc-N-amido-PEG8-alcohol

Structure of 1345337-22-5

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Category
PROTAC Linker
Molecular Formula
C21H43NO10
Molecular Weight
469.57
Related CAS
159156-95-3 (polymer)
Appearance
Pale Yellow or Colorless Oily Liquid

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

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Purity
>97%
Appearance
Pale Yellow or Colorless 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-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl]carbamate
Synonyms
N-Boc-PEG8-alcohol; NHBoc-PEG8-OH; BocNH-PEG8-OH; tert-Butyl (23-hydroxy-3,6,9,12,15,18,21-heptaoxatricosyl)carbamate; 23-(Boc-amino)-3,6,9,12,15,18,21-heptaoxa-1-tricosanol; 2-Methyl-2-propanyl (23-hydroxy-3,6,9,12,15,18,21-heptaoxatricos-1-yl)carbamate; Carbamic acid, N-(23-hydroxy-3,6,9,12,15,18,21-heptaoxatricos-1-yl)-, 1,1-dimethylethyl ester
Density
1.093±0.06 g/cm3 (Predicted)
InChI Key
WHRVSFPIFWXKQZ-UHFFFAOYSA-N
InChI
InChI=1S/C21H43NO10/c1-21(2,3)32-20(24)22-4-6-25-8-10-27-12-14-29-16-18-31-19-17-30-15-13-28-11-9-26-7-5-23/h23H,4-19H2,1-3H3,(H,22,24)
SMILES
CC(C)(C)OC(=O)NCCOCCOCCOCCOCCOCCOCCOCCO

t-Boc-N-amido-PEG8-alcohol is a polyethylene glycol–based linker building block designed for constructing PROTACs and related targeted protein degradation conjugates. Its PEG segment provides conformational flexibility and aqueous compatibility, while the terminal alcohol enables reliable functionalization toward linker-to-ligand attachment. The Boc-protected amide functionality supports controlled coupling strategies that help maintain synthetic fidelity during multistep assembly. Detailed structural and reactivity considerations are provided below.

Structure: This molecule contains a PEG chain terminated by a primary alcohol and an N-amido functionality protected as a Boc carbamate. The structure features ether linkages within the PEG backbone, a carbamate carbonyl, and an amide linkage, offering high polarity and hydrogen-bonding capacity. Overall, it is typically a hydrophilic, flexible linker suitable for bioconjugation.

Reactivity: The terminal alcohol can be converted into activated derivatives (for example, halides, mesylates, or other leaving-group forms) to enable substitution or coupling with nucleophilic partners used in PROTAC synthesis. The Boc-protected amide is commonly deprotected under acid conditions to reveal a reactive amine for subsequent amide- or urea-forming steps. These transformations generally proceed via standard nucleophilic substitution and acylation/carbamate deprotection principles, using inert atmospheres and appropriate anhydrous solvents as required by the chosen coupling chemistry.

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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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