857891-82-8 | O-(2-Aminoethyl)-O′-(2-azidoethyl)heptaethylene glycol

Packsize	Purity	Availability	Price	Discounted Price
50mg	97%	in stock	$122.00	$85.00
100mg	97%	in stock	$131.00	$92.00
250mg	97%	in stock	$211.00	$148.00
500mg	97%	in stock	$290.00	$203.00
1g	97%	in stock	$402.00	$282.00
5g	97%	in stock	$1,078.00	$755.00

Description

• Catalog Number: AB46793
• Chemical Name: O-(2-Aminoethyl)-O′-(2-azidoethyl)heptaethylene glycol
• CAS Number: 857891-82-8
• Molecular Formula: C18H38N4O8
• Molecular Weight: 438.5163
• MDL Number: MFCD03453241
• SMILES: NCCOCCOCCOCCOCCOCCOCCOCCOCCN=[N+]=[N-]

Computed Properties

• Complexity: 376
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 30
• Hydrogen Bond Acceptor Count: 11
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 26
• XLogP3: -1

Upstream Synthesis Route

The upstream synthesis route for O-(2-Aminoethyl)-O′-(2-azidoethyl)heptaethylene glycol involves a multi-step synthetic pathway:

1. Begin with the monomer ethylene oxide, which is subjected to anionic ring-opening polymerization to form heptaethylene glycol.

2. Subsequent protection of the terminal hydroxyl groups can be achieved using a protecting group such as tert-butyldimethylsilyl (TBDMS) chloride with imidazole as base, yielding TBDMS-protected heptaethylene glycol.

3. After protection, selectively deprotect one of the terminal TBDMS groups using tetrabutylammonium fluoride (TBAF) to generate a free hydroxyl group.

4. This free hydroxyl group is then reacted with 2-chloroethanol under basic conditions to introduce the 2-hydroxyethyl group to one end of the heptaethylene glycol chain.

5. The 2-hydroxyethyl end is then converted to an aminoethyl group by reacting with aziridine under acidic conditions, to yield the aminoethyl-heptaethylene glycol intermediate.

6. Subsequent reductive amination can be performed on the aminoethyl-heptaethylene glycol with sodium cyanoborohydride and an azide-containing precursor like 2-azidoacetyl chloride, which introduces the azidoethyl group by reacting with the remaining terminal hydroxyl group on the heptaethylene glycol chain.

7. Finally, deprotection of the TBDMS groups is achieved using TBAF to yield the target molecule, O-(2-Aminoethyl)-O′-(2-azidoethyl)heptaethylene glycol.

During this multi-step synthesis, each step typically requires purification and characterization of intermediates before proceeding to the next. It's crucial to closely monitor reaction conditions such as temperature, pH, and reactant stoichiometry to ensure the proper growth of the heptaethylene glycol chain and accurate functional group transformations.