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

Base Information

• Chemical Name: 1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine
• CAS No.: 182554-04-7
• Molecular Formula: C₁₈H₂₄N₁₂O₉
• Molecular Weight: 552.464
• Mol file: 182554-04-7.mol

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

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

There total 12 articles about 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: 99.0%

para-thiocresol (106-45-6) + acetic acid 2-[3-acetoxy-4-(4,5-diacetoxy-3-azido-6-azidomethyl-tetrahydro-pyran-2-yloxy)-5-hydroxymethyl-tetrahydro-furan-2-yloxy]-4,6-diazido-3-(4,5-diacetoxy-3-azido-6-azidomethyl-tetrahydro-pyran-2-yloxy)-cyclohexyl ester (620172-08-9) → Acetic acid (2S,3R,4R,5R)-4-((2R,3R,4R,5R,6S)-4,5-diacetoxy-3-azido-6-azidomethyl-tetrahydro-pyran-2-yloxy)-5-hydroxymethyl-2-p-tolylsulfanyl-tetrahydro-furan-3-yl ester + 1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine (182554-04-7)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1002/anie.200462003

Reference yield: 90.0%

para-thiocresol (106-45-6) + hexaazido-hepta-O-acetyl neomycin (474266-81-4) → 1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine (182554-04-7) + acetic acid 4-acetoxy-6-(4-acetoxy-2-acetoxymethyl-5-p-tolylsulfanyl-tetrahydrofuran-3-yloxy)-5-azido-2-azidomethyl-tetrahydro-pyran-3-yl ester (474266-82-5)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 25 ℃; for 15h;

DOI:10.1021/ol026548n

Reference yield: 69.0%

acetic anhydride (108-24-7) + 1,3,2′,6′-tetraazidoneamine (671809-10-2) → 1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine (182554-04-7)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jo062369y

upstream raw materials:

acetic anhydride

1,3,2′,6′-tetraazidoneamine

para-thiocresol

hexaazido-hepta-O-acetyl neomycin

Downstream raw materials:

1,3,2',6'-tetraazido-5-O-methoxymethyl-6,3',4'-tri-O-acetylneamine

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

3',4'-di-O-acetyl-5-[[(propylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine

3',4'-di-O-acetyl-6-[[( propylamino)carbonyl]oxy]-1,3,2',6'-tetraazidoneamine

Refernces

• 1、 Granqvist, Lotta,T?htinen, Ville,Virta, Pasi. "Synthesis of glycosidic (β-1′′→6, 3′ and 4′) site isomers of neomycin B and their effect on RNA and DNA triplex stability". . . Retrieved 2019/02/10.
• 2、 Van Den Broek, Sebastiaan A. M. W.,Gruijters, Bas W. T.,Rutjes, Floris P. J. T.,Van Delft, Floris L.,Blaauw, Richard H.. "A short and scalable route to orthogonally O-protected 2-deoxystreptamine". . p. 3577 - 3580. Retrieved 2008/02/04.