Tert-butyl N-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate丨CAS 106984-09-2

tert-butyl N-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate丨CAS 106984-09-2 is a specialized organic compound characterized by a carbamate functional group attached to a tert-butyl protecting group and a polyethylene glycol (PEG)-like chain ending with a hydroxyl group. Its structure lends itself to various applications in organic synthesis, medicinal chemistry, and materials science. 

1. Peptide and Organic Synthesis

Protecting Group in Peptide Chemistry:
The tert-butyl carbamate (Boc) group is widely used to protect amines in peptide synthesis due to its stability under mildly acidic conditions and easy removal under strong acid treatment (e.g., trifluoroacetic acid).
This compound, with a Boc-protected amino group linked to a PEG chain, can serve as a building block for synthesizing peptides and peptidomimetics where enhanced solubility and bioavailability are desired.

PEGylation in Drug Development:
The PEG chain improves water solubility and reduces immunogenicity of drug molecules. This compound can be employed as a linker or modifying agent in PEGylation, attaching PEG units to peptides, proteins, or small molecules to enhance pharmacokinetics.

Intermediate for Functionalization:
The terminal hydroxyl group allows further functionalization such as esterification, etherification, or conjugation to other biomolecules or surfaces, making it versatile in organic synthesis.

2. Pharmaceutical and Medicinal Chemistry

Improving Drug Solubility:
Hydrophobic drugs often suffer from poor solubility and bioavailability. Incorporating PEG chains via compounds like this one can increase solubility and circulation time of drug candidates.

Prodrug Design:
This compound can be used to design prodrugs where the Boc group protects the amine functionality during synthesis, and the PEG chain enhances aqueous solubility. Upon administration, the Boc group can be removed to release the active amine drug.

Conjugation to Targeting Moieties:
The hydroxyl terminus can be conjugated to targeting ligands, antibodies, or nanoparticles to develop targeted drug delivery systems.

3. Materials Science and Polymer Chemistry

Surface Modification:
The PEG segment imparts hydrophilicity and biocompatibility, useful in modifying surfaces of materials such as nanoparticles, biosensors, or medical devices to reduce non-specific protein adsorption and improve biocompatibility.

Crosslinkers and Linkers in Polymer Synthesis:
The compound can act as a linker between polymer chains or as a functional monomer in preparing PEGylated polymers with controlled architectures for biomedical applications.

4. Bioconjugation and Labeling

Attachment to Biomolecules:
The hydroxyl group and the protected amine can be used for selective conjugation reactions to biomolecules such as enzymes, antibodies, or nucleic acids, facilitating labeling or immobilization.

Spacer in Bioconjugates:
The PEG chain acts as a flexible spacer that can reduce steric hindrance and improve the accessibility of active sites in bioconjugates.

1. Enhanced Solubility and Stability

The PEG chain enhances water solubility, which is crucial for biological and pharmaceutical applications.

PEG chains also confer steric protection and reduce protein aggregation, improving stability of conjugates or formulated drugs.

2. Versatile Synthetic Utility

The Boc protecting group allows selective deprotection under mild acidic conditions, enabling multi-step syntheses without unwanted side reactions.

The terminal hydroxyl provides a reactive handle for further chemical modifications, making the compound a versatile intermediate.

3. Biocompatibility

PEG is well-known for its low toxicity and immunogenicity, improving the safety profile of PEGylated molecules.

The compound can be used in the design of biocompatible drug conjugates or materials, expanding its utility in medical applications.

4. Improved Pharmacokinetics

PEGylation of drug molecules improves their half-life by reducing renal clearance and proteolytic degradation.

This compound facilitates incorporation of PEG into drugs or peptides, helping to optimize their pharmacokinetic profiles.

5. Controlled Functionalization

The presence of both a protected amine and a hydroxyl group allows for orthogonal chemistry strategies in complex syntheses.

Enables the design of multifunctional molecules for diverse applications such as targeted delivery, imaging, or diagnostic assays.

tert-butyl N-(2-(2-(2-(2-hydroxyethoxy)ethoxy)ethoxy)ethyl)carbamate丨CAS 106984-09-2 is a multifunctional compound combining a Boc-protected amine with a PEG chain ending in a hydroxyl group. Its applications range across:

Peptide synthesis as a protecting group and PEGylation reagent,

Pharmaceutical development for improving solubility and drug delivery,

Materials science for surface modification and polymer chemistry,

Bioconjugation for labeling and creating biocompatible conjugates.

The key benefits include enhanced solubility, synthetic versatility, biocompatibility, and improved pharmacokinetics, making this compound valuable in advanced organic synthesis and drug development workflows.