20379-60-6

Basic information

• Product Name: a-D-Glucopyranosylazide
• Synonyms: a-D-Glucopyranosylazide;alpha-D-Glucopyranosyl azide
• CAS NO: 20379-60-6
• Molecular Formula: C₆H₁₁N₃O₅
• Molecular Weight: 0
• Mol File: 20379-60-6.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: a-D-Glucopyranosylazide(CAS DataBase Reference)
• NIST Chemistry Reference: a-D-Glucopyranosylazide(20379-60-6)
• EPA Substance Registry System: a-D-Glucopyranosylazide(20379-60-6)

Safety Data

• Hazardous Substances Data: 20379-60-6(Hazardous Substances Data)

Upstream product

• 2641-79-4 methyl 2,3,4,6-tetrakis-O-trimethylsilyl-α-D-glucopyranoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 50-99-7 D-glucose 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 20379-61-7 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl azide 
• 13992-25-1 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 
• 2280-44-6 D-Glucose 

Downstream Products

• 85917-82-4 1-azido-1-deoxy-2,3,4,6-tetra-O-benzyl-α-D-glucopyranose 
• 1263322-18-4 C₁₆H₂₂N₂O₈ 
• 1202249-80-6 N-(N-benzyloxycarbonylglycyl)-α-D-glucopyranosylamine 
• 1202249-79-3 N-(N-benzyloxycarbonyl-β-alanyl)-α-D-glucopyranosylamine 
• 1046453-75-1 Nα-benzyloxycarbonyl-Nγ-α-D-glucopyranosyl-L-glutamine-O-methyl ester 
• 1046453-74-0 Nα-benzyloxycarbonyl-Nγ-α-D-glucopyranosyl-L-asparagine-O-methyl ester 
• 131088-71-6 2,3-di-O-benzyl-4,6-O-isopropylidene-α-D-glucopyranosyl azide 
• 131088-72-7 2,3-di-O-benzyl-4,6-O-isopropylidene-α,β-D-glucopyranosylamine 
• 80977-08-8 O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<*>6)-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-acetyl-N-(O-ethyl-N-benzyloxycarbonyl-L-β-aspartyl)-α-D-glucopyranosylamine 
• 80977-08-8 O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<*>6)-O-(2,3,4-tri-O-acel-β-D-glucopyranosyl)-(1<*>6)-(2,3,4-tri-O-acetyl-N-)O-ethyl-N-(O-ethyl-N-benzyloxycarbonyl-L-β-aspartyl)-β-D-glucopyranosylamine 
• 77437-53-7 O-(α-D-glucopyranosyl)-(1<*>6)-O-β-D-glucopyranosyl-(1<*>6)-N-(L-β-aspartyl)-β-D-glucopyranosylamine 
• 77437-53-7 O-(α-D-glucopyranosyl)-(1<*>6)-O-β-D-glucopyranosyl-(1<*>6)-N-(L-β-aspartyl)-α-D-glucopyranosylamine 
• 82557-32-2 C₃₁H₃₅N₃O₁₀ 
• 85917-83-5 1-amino-2,3,4,6-tetra-O-benzyl-1-deoxy-α-D-glucopyranose 

Relevant articles and documents

On-Chip Neo-Glycopeptide Synthesis for Multivalent Glycan Presentation

Single glycan–protein interactions are often weak, such that glycan binding partners commonly utilize multiple, spatially defined binding sites to enhance binding avidity and specificity. Current array technologies usually neglect defined multivalent display. Laser-based array synthesis technology allows for flexible and rapid on-surface synthesis of different peptides. By combining this technique with click chemistry, neo-glycopeptides were produced directly on a functionalized glass slide in the microarray format. Density and spatial distribution of carbohydrates can be tuned, resulting in well-defined glycan structures for multivalent display. The two lectins concanavalin A and langerin were probed with different glycans on multivalent scaffolds, revealing strong spacing-, density-, and ligand-dependent binding. In addition, we could also measure the surface dissociation constant. This approach allows for a rapid generation, screening, and optimization of a multitude of multivalent scaffolds for glycan binding.

Switching between X-Pyrano-, X-Furano-, and Anhydro- X-pyranoside Synthesis (X = C, N) under Lewis acid Catalyzed Conditions

A variety of C-glycosides can be obtained from the fluoroarylborane (B(C6F5)3) or silylium (R3Si+) catalyzed functionalization of 1-MeO- and per-TMS-sugars with TMS-X reagents. A one-step functionalization with a change as simple as the addition order and/or Lewis acid and TMS-X enables one to afford chiral synthons that are common (C-pyranosides), have few viable synthetic methods (C-furanosides), or are virtually unknown (anhydro-C-pyranosides), which mechanistically arise from whether a direct substitution, isomerization/substitution, or substitution/isomerization occurs, respectively.

Synthesis of (-)-epigallocatechin-3-gallate derivative containing a triazole ring and combined with cisplatin/paclitaxel inhibits NSCLC cancer cells by decreasing phosphorylation of the EGFR

Non-small-cell lung cancer is one of the principal causes of cancer-related death around the world. Chemotherapy is commonly used to treat wild type of epidermal growth factor receptor non-small-cell lung cancer. (-)-Epigallocatechin-3-gallate is the most abundant and active catechin. However, (-)-epigallocatechin-3-gallate has limited clinical application due to its poor stability and absorption. Herein, we report that a glycosylated azide undergoes a click reaction with the terminal alkyne of (-)-epigallocatechin-3-gallate to yield a triazole-linked glucose-(-)-epigallocatechin-3-gallate derivative and have evaluated its in vitro anticancer activity against human non-small-cell lung cancer cells using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. The product inhibits human non-small-cell lung cancer cell lines with wild type of epidermal growth factor receptor and in combination with cisplatin/paclitaxel results in more pronounced proliferation inhibition than when used alone. Stability investigations indicates that the conjugated glucose residue can improve the stability of the (-)-epigallocatechin-3-gallate scaffold. Our studies suggest that the combination of the glucose-(-)-epigallocatechin-3-gallate derivative and chemotherapeutic drugs may provide a novel strategy for the treatment of non-small-cell lung cancer.

Direct azidation of unprotected carbohydrates under Mitsunobu conditions using hydrazoic acid

A single step procedure for the direct and regioselective synthesis of carbohydrate azides from unprotected sugars using hydrazoic acid under Mitsunobu conditions is reported. A series of mono-, di-, or triazido polyhydroxylated systems are described.

Efficient synthesis of "star-like" surfactants via "click chemistry" [3+2] copper (I)-catalyzed cycloaddition

We report an efficient synthesis of tetra- and hexa-substituted carbohydrate-coated compounds, which we have named "star-like" surfactants, starting from either α-methylglucose or myo-inositol as a central core. The synthesis explores a new approach to su

Neighbouring group participation of C-6 substituents of glucose derivatives on the stereoselectivity of the N-glycosidic linkage of glycopeptides

The first example of a glycopeptide with a direct N-α-glycosidic linkage between the trisaccharide and the amino acid residue was found in the glomerular basement membrane of rats. In connection with the total synthesis of nephritogenoside, glycosyl azides with different protecting groups and carbohydrate chain lengths are synthesized, reduced to the corresponding glycosyl amines and coupled with Z-Asp-OBzl. Remarkable differences in the α:β ratio of the condensation products are observed, caused by neighbouring group participation.

Facile Syntheses of Galacto- and Glucopyranosyl Azides Substituted at C-6

Acetylated 6-chloro-, 6-bromo-, 6-iodo-, and 6-azido-6-deoxy-α-D-glucopyranosyl azides (26, 22, 17, 30), -β-D-glucopyranosyl azides (27, 23, 18, 31), -α-D-galactopyranosyl azides (28, 24, 19, 32), and -β-D-galactopyranosyl azides (29, 25, 20, 33) have been obtained by nucleophilic displacement reactions of the appropriate 6-O-(p-toluenesulfonates) 9-12.Hydrogen iodide elimination from the 6-iodo-6-deoxyglycosyl azides 17-20 by DBU or DBN leads to the hex-5-enopyranosyl azides with α-D-xylo (43), β-D-xylo (44), α-L-arabino (46), and β-L-arabino configuration.The. structures, anomeric configurations, and conformations of the products were determined by 1H-NMR spectroscopy