80321-89-7

Basic information

• Product Name: 1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-BETA-D-GLUCOPYRANOSE
• Synonyms: TAAD;β-D-Glucopyranose, 2-azido-2-deoxy-, 1,3,4,6-tetraacetate;1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-β-D-glucopyranose ,97%;2-Azido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl acetate;2-Azido-β-D-glucose tetraacetate;1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-β1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-BETA-D-GLUCOPYRANOSE;2-AZIDO-2-DEOXY-1,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSE
• CAS NO: 80321-89-7
• Molecular Formula: C₁₄H₁₉N₃O₉
• Molecular Weight: 373.32
• Product Categories: Aliphatic Azides;Alkynes and Other Reagents;Azides;Building Blocks;Carbohydrate Azides;Carbohydrate Chemistry;Carbohydrate Derivatives;Chemical Biology;Chemical Synthesis;Conjugation Chemistry: Azides;Nitrogen Compounds;Organic Building Blocks;Biochemistry;Glucose;O-Substituted Sugars;Sugars
• Mol File: 80321-89-7.mol
• Article Data: 2

Chemical Properties

• Melting Point: 97 °C
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: g/cm³
• Storage Temp.: Freezer
• CAS DataBase Reference: 1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-BETA-D-GLUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-BETA-D-GLUCOPYRANOSE(80321-89-7)
• EPA Substance Registry System: 1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-BETA-D-GLUCOPYRANOSE(80321-89-7)

Safety Data

• Hazard Codes: Xn
• Statements: 20/21/22-36/37/38-68
• Safety Statements: 26-36/37
• Hazardous Substances Data: 80321-89-7(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder

InChI:InChI=1/C14H19N3O9/c1-6(18)22-5-10-12(23-7(2)19)13(24-8(3)20)11(16-17-15)14(26-10)25-9(4)21/h10-14H,5H2,1-4H3/t10-,11-,12-,13-,14-/m1/s1

Upstream product

• 127-09-3 sodium acetate 
• 668481-16-1 Acetic acid (2R,3S,4R)-4-acetoxy-2-acetoxymethyl-5-azido-6-nitrooxy-tetrahydro-pyran-3-yl ester 
• 1600-27-7 mercury(II) diacetate 
• 2873-29-2 D-glucal triacetate 

Downstream Products

• 166907-09-1 (2R,3S,4R,5R)-5-azido-6-(benzyloxy)-2-(hydroxymethyl)tetrahydro-2H-pyran-3,4-diol 
• 484-57-1 (R)-2-(((3R,4R,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)propanoic acid 
• 17460-45-6 tetra-acetyl glucosamine 
• 146934-31-8 Methyl 2-azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-1-thio-α-D-glucopyranoside 
• 146934-32-9 2-Azido-4,6-O-benzylidene-3-O-chloroacetyl-2-deoxy-β-D-glucopyranosyl chloride 
• 146934-30-7 Methyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-glucopyranoside 
• 296769-05-6 4-chlorophenyl 2-azido-3,4,6-tri-O-benzoyl-2-deoxy-1-thio-α-D-glucopyranoside 

Relevant articles and documents

Investigating cellular metabolism of synthetic azidosugars with the Staudinger ligation

The structure of sialic acid on living cells can be modulated by metabolism of unnatural biosynthetic precursors. Here we investigate the conversion of a panel of azide-functionalized mannosamine and glucosamine derivatives into cell-surface sialosides. A key tool in this study is the Staudinger ligation, a highly selective reaction between modified triarylphosphines and azides that produces an amide-linked product. A preliminary study of the mechanism of this reaction, and refined conditions for its in vivo execution, are reported. The reaction provided a means to label the glycoconjugate-bound azidosugars with biochemical probes. Finally, we demonstrate that the cell-surface Staudinger ligation is compatible with hydrazone formation from metabolically introduced ketones. These two strategies provide a means to selectively modify cell-surface glycans with exogenous probes.