134179-38-7 | 1-Amino-11-azido-3,6,9-trioxaundecane

Packsize	Purity	Availability	Price	Discounted Price
100mg	95%	in stock	$18.00	$12.00
250mg	95%	in stock	$30.00	$21.00
1g	95%	in stock	$115.00	$80.00
5g	95%	in stock	$123.00	$87.00
25g	95%	in stock	$311.00	$218.00

Description

• Catalog Number: AB57723
• Chemical Name: 1-Amino-11-azido-3,6,9-trioxaundecane
• CAS Number: 134179-38-7
• Molecular Formula: C8H18N4O3
• Molecular Weight: 218.25352000000004
• MDL Number: MFCD00269874
• SMILES: NCCOCCOCCOCCN=[N+]=[N-]

Computed Properties

• Complexity: 173
• Covalently-Bonded Unit Count: 1
• Heavy Atom Count: 15
• Hydrogen Bond Acceptor Count: 6
• Hydrogen Bond Donor Count: 1
• Rotatable Bond Count: 11
• XLogP3: -0.3

Upstream Synthesis Route

To synthesize 1-Amino-11-azido-3,6,9-trioxaundecane, the following upstream synthetic route can be employed:

1. Start with the commercially available 1,11-dibromo-3,6,9-trioxaundecane as the precursor.
2. Conduct a nucleophilic substitution reaction of one bromo group with sodium azide to introduce the azido functional group, yielding 11-azido-3,6,9-trioxaundecan-1-ol.
3. Protect the hydroxyl group using an appropriate protecting group such as tert-butyldimethylsilyl chloride (TBDMS-Cl) in the presence of imidazole to produce TBDMS-protected 11-azido-3,6,9-trioxaundecane.
4. Perform a nucleophilic substitution of the remaining bromo group with sodium azide in the presence of a base such as sodium hydride (NaH), obtaining the bis-azide intermediate.
5. Remove the protecting group using a fluoride source like tetra-n-butylammonium fluoride (TBAF) to yield 1-azido-11-azido-3,6,9-trioxaundecane.
6. Finally, reduce one azido group to the amino group using a suitable reducing agent such as lithium aluminum hydride (LiAlH4) or a Staudinger reduction with triphenylphosphine to achieve the desired 1-Amino-11-azido-3,6,9-trioxaundecane.

Ensure proper handling of reagents and control of reaction conditions at each step for selectivity and to maximize yield.

Literature

• Protein sulfenation as a redox sensor: proteomics studies using a novel biotinylated dimedone analogue.

  Molecular & cellular proteomics : MCP 20070901

• Design of biotin-functionalized luminescent quantum dots.

  Journal of biomedicine & biotechnology 20070101