1,3,4,6-tetra-O-acetyl-2-N-azidoacetyl-2-deoxy-β-D-glucopyranose

Base Information

• Chemical Name: 1,3,4,6-tetra-O-acetyl-2-N-azidoacetyl-2-deoxy-β-D-glucopyranose
• CAS No.: 653600-56-7
• Molecular Formula: C₁₆H₂₂N₄O₁₀
• Molecular Weight: 430.371

Synonyms:

Chemical Property of 1,3,4,6-tetra-O-acetyl-2-N-azidoacetyl-2-deoxy-β-D-glucopyranose

Chemical Property:

Purity/Quality:

97% ^*data from raw suppliers

N-azidoacetylgalactosamine-tetraacylated(Ac4GalNAz),90% 90% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: The unnatural azido-containing monosaccharide building block. The azide moiety can be used for modification though chemoselective ligation chemistries including CuAAC, Cu-free click reaction or Staudinger ligation. The acetyl groups increase solubility in many solvents and make handling of this reagent easier.
• Uses: N-Azidoacetylgalactosamine-tetraacylated (Ac4GalNAz) provides the first part of a simple and robust two-step technique that helps identify and characterize cell surface sialic acid-containing glycoproteins. The azide-modified protein can be detected by reaction with alkynes. For example alkynes labeled with a fluorescent probe or a biotin can be used. The acetyl groups increase cell permeability and allow the unnatural sugars to easily pass through the cell membrane. Carboxyesterases remove the acetyl groups once the monosaccharide is in the cell.

Technology Process of 1,3,4,6-tetra-O-acetyl-2-N-azidoacetyl-2-deoxy-β-D-glucopyranose

There total 26 articles about 1,3,4,6-tetra-O-acetyl-2-N-azidoacetyl-2-deoxy-β-D-glucopyranose 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: 95.0%

acetic anhydride (108-24-7) + 2-(azidoacetamido)-2-deoxy-D-mannopyranose → 1,3,4,6-tetra-O-acetyl-2-azidoacetylamido-2-deoxy-α,β-D-mannopyranose (653600-56-7,98924-81-3,1404472-50-9)

Guidance literature:

With pyridine; dmap; at 0 - 20 ℃; for 10h;

DOI:10.1021/ja027748x

Reference yield: 91.0%

1,3,4,6-tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranoside (68499-56-9) → 1,3,4,6-tetra-O-acetyl-2-azidoacetamide-2-deoxy-β-D-glucopyranose (857677-98-6,653600-56-7,98924-81-3,1404472-50-9)

Guidance literature:

With sodium azide;

DOI:10.1080/10426507.2017.1311332

Reference yield: 84.0%

N-azidoacetylgalactosamine + acetic anhydride (108-24-7) → 1,3,4,6-tetra-O-acetyl-2-deoxy-2-azidoacetylamino-D-galactopyranose (653600-56-7,98924-81-3,1404472-50-9)

Guidance literature:

With pyridine;

DOI:10.1021/ja104547x

upstream raw materials:

2-azidoacetyl chloride

tetra-acetyl glucosamine

1,3,4,6-tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranoside

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(4-methoxybenzylidene)amino-β-D-glucopyranose

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