Name: Amino-PEG2-t-butyl acetate
Brand: BOC Sciences
Rating: 5 (1 reviews)

Size

Price

Stock

Quantity

$--

In stock

Purity

>95%

Appearance

Transparent Liquid

Storage

Store at 2-8°C

Shipping

Room temperature in continental US; may vary elsewhere.

IUPACName

tert-butyl 2-[2-(2-aminoethoxy)ethoxy]acetate

Synonyms

8-Amino-3,6-dioxaoctanoic Acid tert-butyl Ester; H2N-PEG2-CH2COOtBu

Boiling Point

297.4±20.0°C (Predicted)

Density

1.026±0.06 g/cm3 (Predicted)

InChI Key

WFBRWOZVLSLRSZ-UHFFFAOYSA-N

InChI

InChI=1S/C10H21NO4/c1-10(2,3)15-9(12)8-14-7-6-13-5-4-11/h4-8,11H2,1-3H3

SMILES

CC(C)(C)OC(=O)COCCOCCN

1. Acetal-Based Functional Epoxide Monomers: Polymerizations and Applications

Jinsu Baek, Minseong Kim, Youngsin Park, Byeong-Su Kim Macromol Biosci. 2021 Nov;21(11):e2100251.doi: 10.1002/mabi.202100251.Epub 2021 Aug 8.

Protecting group chemistry is essential for various organic transformation and polymerization processes. In particular, conventional anionic ring-opening polymerization (AROP) often requires proper protecting group chemistry because it is typically incompatible with most functional groups due to the highly basic and nucleophilic conditions. In this context, many functional epoxide monomers with proper protecting groups are developed, including the acetal group as a representative example. Since the early introduction of ethoxyethyl glycidyl ether, there is significant development of acetal-based monomers in the polyethers. These monomers are now utilized not only as protecting groups for hydroxyl groups under AROP conditions but also as pH-responsive moieties for biomedical applications, further expanding their utility in the use of functionalized polyethers. Recent progress in this field is outlined from their synthesis, polymerization, and biomedical applications.

2. Photoacid-catalyzed acetalization of carbonyls with alcohols

Jason Saway, Abigail F Pierre, Joseph J Badillo Org Biomol Chem. 2022 Aug 10;20(31):6188-6192.doi: 10.1039/d2ob00435f.

In this report, we demonstrate that visible light photoactivation of 6-bromo-2-naphthol facilitates the photoacid-catalyzed acetalization of carbonyls with alcohols. We also demonstrate that 2-naphthol when coupled to a photosensitizer provides acetals from electron-deficient aldehydes. In addition, the S1 excited state pKa for 6-bromo-2-naphthol in water was determined and shown to have increased excited-state acidity relative to 2-naphthol.

3. Chemistry and biology of spiroacetals from myxobacteria

Michael Ricca, Mark A Rizzacasa Org Biomol Chem. 2021 Apr 7;19(13):2871-2890.doi: 10.1039/d1ob00026h.Epub 2021 Mar 8.

This review details the isolation, biosynthesis, biological activity and synthesis of spiroacetals from the myxobacterium Sorangium cellulosum. The strategies utilised to access the challenging structures and stereochemistry of these natural products are highlighted.

Amino-PEG2-t-butyl acetate is a PEG-based, amino-functional linker designed for assembling PROTAC constructs in which controlled spacing and aqueous compatibility are beneficial for efficient ternary complex formation. Its protected t-butyl acetate functionality supports modular synthesis, while the amino handle enables coupling to targeting ligands or reactive intermediates. The linker’s flexible ether-rich backbone can improve solubility and facilitate rational linker-length tuning; the following points describe its structure and practical reactivity considerations in detail below.

Structure: The linker contains an amino group and a short poly(ethylene glycol) segment, incorporating ether linkages that provide conformational flexibility and hydrophilicity. A t-butyl acetate moiety provides an ester functionality for protection and later deprotection chemistry. Overall, it is a polar, ether-containing organic molecule with an ester and an amine.

Reactivity: The amino functionality is suitable for standard amide or carbamate-forming coupling strategies with activated carboxylic acids or electrophilic derivatives under mild base or coupling conditions. The t-butyl acetate ester can be cleaved under acidic conditions to reveal the corresponding alcohol for subsequent conjugation steps, following established tert-butyl ester deprotection principles. Typical workflows use dry organic solvents for coupling and aqueous/organic mixtures for solubility management, with acid or base selected to preserve other functional groups during sequential assembly.

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* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C₁V₁ = C₂V₂