516493-93-9 | 17-Azido-3,6,9,12,15-pentaoxaheptadecan-1-amine

Packsize	Purity	Availability	Price	Discounted Price
1g	95%	in stock	$89.00	$62.00
5g	95%	in stock	$322.00	$225.00
25g	95%	in stock	$1,224.00	$857.00

Description

• Catalog Number: AG23756
• Chemical Name: 17-Azido-3,6,9,12,15-pentaoxaheptadecan-1-amine
• CAS Number: 516493-93-9
• Molecular Formula: C12H26N4O5
• Molecular Weight: 306.35864000000004
• MDL Number: MFCD16619318
• SMILES: NCCOCCOCCOCCOCCOCCN=[N+]=[N-]

Computed Properties

• Complexity: 252
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 21
• Hydrogen Bond Acceptor Count: 8
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 17
• XLogP3: -0.5

Upstream Synthesis Route

To synthesize 17-Azido-3,6,9,12,15-pentaoxaheptadecan-1-amine, one can start from 1,16-hexadecanediol as the backbone compound. Proceed with the following steps:

1. Activation of the alcohol groups on 1,16-hexadecanediol by converting them to tosylates using p-Toluenesulfonyl chloride (TsCl) in the presence of a base like pyridine or triethylamine.

2. Nucleophilic substitution of one tosyl group with azide anion by reacting the tosylated hexadecanediol with sodium azide (NaN3) to form the monoazido derivative.

3. Using Williamson ether synthesis, perform consecutive etherifications of the remaining tosyl group with ethylene glycol. This can be done multiple times until the pentaoxa chain is completed, forming the desired 17-Azido-3,6,9,12,15-pentaoxaheptadecane.

4. Finally, introduce the amine functionality at the terminus of the molecule by reacting the 17-azido pentaoxa compound with excess ammonia (NH3), under pressure if needed, to replace the terminal hydroxyl group with an amine, yielding 17-Azido-3,6,9,12,15-pentaoxaheptadecan-1-amine.

This synthesis route involves basic organic transformations including tosylation, nucleophilic substitution, Williamson ether synthesis, and amine introduction by substitution, which should be performed under anhydrous conditions to optimize yields and prevent side reactions.