1056024-94-2 | Azido-PEG3-acid

Packsize	Purity	Availability	Price	Discounted Price
250mg	95%	in stock	$58.00	$41.00
1g	95%	in stock	$121.00	$85.00
5g	95%	in stock	$315.00	$221.00
25g	95%	in stock	$1,547.00	$1,083.00

Description

• Catalog Number: AE27990
• Chemical Name: Azido-PEG3-acid
• CAS Number: 1056024-94-2
• Molecular Formula: C9H17N3O5
• Molecular Weight: 247.2484
• MDL Number: MFCD23726617
• SMILES: [N-]=[N+]=NCCOCCOCCOCCC(=O)O

Computed Properties

• Complexity: 243
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 17
• Hydrogen Bond Acceptor Count: 7
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 12
• XLogP3: 0.2

Upstream Synthesis Route

To synthesize Azido-PEG3-acid, one starts with the readily available molecule, 3,6,9-trioxaundecanedioic acid, which contains the desired PEG3 (polyethylene glycol with three ethylene glycol units) segment flanked with carboxylic acid functionalities.

Step 1: Activation of Carboxylic Acid
One carboxylic acid group is activated using a coupling agent such as DCC (Dicyclohexylcarbodiimide) or EDC (1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide) in the presence of a catalyst like DMAP (4-Dimethylaminopyridine). This step converts the carboxylic acid to an active ester or an amide, enhancing its reactivity for the subsequent substitution reaction.

Step 2: Introduction of Azide Group
The activated ester or amide then undergoes nucleophilic substitution with an azide salt, such as sodium azide (NaN3), leading to the replacement of the leaving group with the azide functionality, yielding the azido-PEG3 intermediate.

Step 3: Deprotection of the Second Carboxylic Acid
In cases where the protected form of 3,6,9-trioxaundecanedioic acid is used (e.g., using protecting groups like methyl or t-butyl esters), the unprotected PEG3-acid may already have one free carboxylic acid ready for modification. Otherwise, a deprotection step of the second ester group is necessary to yield the free carboxylic acid. This can usually be accomplished via hydrolysis under acidic or basic conditions.

Step 4: Purification
The resultant product, azido-PEG3-acid, is typically purified using chromatographic techniques such as column chromatography or preparative HPLC to remove any side-products or unreacted starting materials.

Throughout the synthesis, analytical techniques like NMR (Nuclear Magnetic Resonance), IR (Infrared Spectroscopy), and Mass Spectrometry are used to verify the structure and purity of intermediates and the final product.