5-[(chlorocarbonyl)oxy]-1,3,2',6'-tetraazido-6,3',4'-tri-O-acetylneamine

Base Information

• Chemical Name: 5-[(chlorocarbonyl)oxy]-1,3,2',6'-tetraazido-6,3',4'-tri-O-acetylneamine
• CAS No.: 1383687-90-8
• Molecular Formula: C₁₉H₂₃ClN₁₂O₁₀
• Molecular Weight: 614.919
• Mol file: 1383687-90-8.mol

Synonyms:5-[(chlorocarbonyl)oxy]-1,3,2',6'-tetraazido-6,3',4'-tri-O-acetylneamine

Chemical Property of 5-[(chlorocarbonyl)oxy]-1,3,2',6'-tetraazido-6,3',4'-tri-O-acetylneamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-[(chlorocarbonyl)oxy]-1,3,2',6'-tetraazido-6,3',4'-tri-O-acetylneamine

There total 2 articles about 5-[(chlorocarbonyl)oxy]-1,3,2',6'-tetraazido-6,3',4'-tri-O-acetylneamine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 84.0%

bis(trichloromethyl) carbonate (32315-10-9) + 1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine (182554-04-7) → 5-[(chlorocarbonyl)oxy]-1,3,2',6'-tetraazido-6,3',4'-tri-O-acetylneamine (1383687-90-8)

Guidance literature:

With pyridine; In dichloromethane; Inert atmosphere;

DOI:10.1039/c2ob07065k

Reference yield:

neomycin A (3947-65-7) → 5-[(chlorocarbonyl)oxy]-1,3,2',6'-tetraazido-6,3',4'-tri-O-acetylneamine (1383687-90-8)

Guidance literature:

Multi-step reaction with 3 steps

1: triflic azide; copper(II) sulfate; triethylamine

2: pyridine / dichloromethane / 2 h / 0 - 20 °C

3: pyridine / dichloromethane / Inert atmosphere

With pyridine; triflic azide; copper(II) sulfate; triethylamine; In dichloromethane;

DOI:10.1039/c2ob07065k

Reference yield: 93.0%

3-azidopropylamine (88192-19-2) + 5-[(chlorocarbonyl)oxy]-1,3,2',6'-tetraazido-6,3',4'-tri-O-acetylneamine (1383687-90-8) → 5-[[(3-azidopropylamino)carbonyl]oxy]-1,3,2',6'-tetraazido-6,3',4'-tri-O-acetylneamine (1383687-91-9)

Guidance literature:

In dichloromethane; at 20 ℃; for 2h;

DOI:10.1039/c2ob07065k

upstream raw materials:

bis(trichloromethyl) carbonate

1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine

neomycin A

Downstream raw materials:

5-[[(3-azidopropylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine

5-[[(3-azidopropylamino)carbonyl]oxy]-1,3,2',6'-tetraazido-6,3',4'-tri-O-acetylneamine