56883-33-1

Basic information

• Product Name: 1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSE
• Synonyms: 2-AZIDO-2-DEOXY-1,3,4,6-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSE;1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSE;Tetraacetylazidodeoxyglucopyranose
• CAS NO: 56883-33-1
• Molecular Formula: C₁₄H₁₉N₃O₉
• Molecular Weight: 373.32
• Product Categories: Biochemistry;Glucose;O-Substituted Sugars;Sugars
• Mol File: 56883-33-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• CAS DataBase Reference: 1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSE(56883-33-1)
• EPA Substance Registry System: 1,3,4,6-TETRA-O-ACETYL-2-AZIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSE(56883-33-1)

Safety Data

• Hazardous Substances Data: 56883-33-1(Hazardous Substances Data)

Usage

Chemical Properties

White to off-white powder or crystal

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 
• 2873-29-2 D-glucal triacetate 
• 1600-27-7 mercury(II) diacetate 

Downstream Products

• 183875-35-6 phenyl 3,4,6-tri-O-acetyl-2-deoxy-2-azido-1-thiol-α-D-glucopyranoside 
• 1394857-58-9 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranosyl-(1-4)-methyl-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate 
• 915154-75-5 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl-2-O-acetyl-3-O-benzyl-1-O-trichloroacetimidate-α/β-L-idopyranuronate 
• 1394857-56-7 methyl (phenyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl)-2-O-benzoyl-3-O-benzyl-1-thio-β-L-idopyranoside)-uronate 
• 1394857-49-8 methyl (phenyl 4-O-(6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl)-2-O-acetyl-3-O-benzyl-1-thio-α-L-idopyranoside)-uronate 
• 1394857-46-5 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-methyl 1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronate 
• 1394857-44-3 6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-α-D-glucopyranosyl-(1-4)-1,2-di-O-acetyl-3-O-benzyl-β-L-idopyranuronamide 
• 1394857-43-2 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-1-O-trichloroacetimidate-α-D-glucopyranoside 
• 1394857-61-4 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-p-methoxybenzyl-1-O-trichloroacetimidate-β-D-glucopyranoside 
• 1200833-56-2 C₄₉H₅₁Cl₃N₄O₁₅ 
• 116265-22-6 Benzyl-2,3,5,6-tetra-O-benzyl-7-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-α-D-glucopyranosyl)-L-glycero-α-D-manno-heptofuranosid 
• 116265-23-7 Benzyl-2,3,5,6-tetra-O-benzyl-7-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-β-D-glucopyranosyl)-L-glycero-α-D-manno-heptofuranosid 
• 116278-44-5 (2R,3S,4R,5R,6S)-5-Azido-6-[(2S,3R)-2,3-bis-benzyloxy-3-((2R,3S,4S,5S)-3,4,5-tris-benzyloxy-tetrahydro-furan-2-yl)-propoxy]-2-hydroxymethyl-tetrahydro-pyran-3,4-diol 
• 116278-43-4 (2R,3S,4R,5R,6R)-5-Azido-6-[(2S,3R)-2,3-bis-benzyloxy-3-((2R,3S,4S,5S)-3,4,5-tris-benzyloxy-tetrahydro-furan-2-yl)-propoxy]-2-hydroxymethyl-tetrahydro-pyran-3,4-diol 

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.

ADDITION OF HALOGENOAZIDES TO GLYCALS

Addition of chloroazide to 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-lyxo- (1) and -D-arabino-hex-1-enitol (2) under u.v. irradiation proceeds regio- and stereo-selectively yielding mainly O-acetyl derivatives of 2-azido-2-deoxy-D-galactopyranose and -D-glucopyranose, respectively. 3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl azide and 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-talopyranose (from 1), and 1,3,4,6-tetra-O-acetyl-2-chloro-2-deoxy-α-D-glucopyranosyl azide and 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranose (from 2) are byproducts. 1,5-Anhydro-3,4,6-tri-O-benzyl-2-deoxy-D-lyxo- and -D-arabino-hex-1-enitol reacted more rapidly with chloroazide, to give, under irradiation, derivatives of 2-azido-2-deoxy-D-galactose and -D-glucose, respectively.However, reaction in the dark gave mainly O-benzyl derivatives of 2-chloro-2-deoxy-α-D-galacto- and -α-D-glucopyranosyl azide.The difference between the products obtained may depend on the existence of two parallel processes, one radical (under irradiation), and the other ionic (reaction in the dark).