13992-25-1

Basic information

• Product Name: 1-AZIDO-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOSE
• Synonyms: 2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOPYRANOSYL AZIDE;2,3,4,6-TETRA-O-ACETYL-1-DEOXY-BETA-D-GLUCOPYRANOSYL AZIDE;1-AZIDO-1-DEOXY-BETA-D-GLUCOPYRANOSIDE TETRAACETATE;1-AZIDO-2,3,4,6-O-ACETYL-BETA-D-GLUCOSE;1-AZIDO-2,3,4,6-TETRA-O-ACETYL-B-D-GLUCOSE;1-AZIDO-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOSE;1-Azido-2,3,4,6-tetra-O-acetyl-D-glucose;1-azido-1-deoxy-β-d-glucopyranoside tetraacetate
• CAS NO: 13992-25-1
• Molecular Formula: C₁₄H₁₉N₃O₉
• Molecular Weight: 373.32
• Product Categories: Sugars, Carbohydrates & Glucosides;MonosaccharidesChemical Ligation;Carbohydrate Synthesis;Click Chemistry;Organic Azides;Specialty Synthesis;Carbohydrates
• Mol File: 13992-25-1.mol

Chemical Properties

• Melting Point: 127-131 °C(lit.)
• Boiling Point: 502.57°C (rough estimate)
• Appearance: White to beige crystalline powder
• Density: 1.3271 (rough estimate)
• Refractive Index: 1.5700 (estimate)
• CAS DataBase Reference: 1-AZIDO-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOSE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-AZIDO-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOSE(13992-25-1)
• EPA Substance Registry System: 1-AZIDO-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOSE(13992-25-1)

Safety Data

• Hazard Codes: Xi
• Statements: 2-11
• Safety Statements: 22-24/25
• RIDADR: 1325
• WGK Germany: 3
• Hazardous Substances Data: 13992-25-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
1-AZIDO-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOSE is used as an intermediate for the synthesis of Protein Tyrosine Phosphatase 1B inhibitors. These inhibitors play a crucial role in regulating cellular signaling pathways and have potential applications in the treatment of various diseases, including diabetes and obesity.
Used in Bioconjugation and Drug Delivery:
1-AZIDO-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOSE is used as a building block for the preparation of variously coupled conjugates of D-glucose via click chemistry. These conjugates are employed in the inhibition of glycogen phosphorylase, an enzyme involved in the regulation of glucose metabolism. By targeting this enzyme, these conjugates have potential applications in the development of therapies for metabolic disorders and other conditions related to glucose metabolism.
Used in Research and Development:
1-AZIDO-2,3,4,6-TETRA-O-ACETYL-BETA-D-GLUCOSE is also used as a valuable tool in research and development, particularly in the fields of biochemistry, molecular biology, and drug discovery. Its unique chemical properties and reactivity make it an essential component in the synthesis of novel compounds and the development of new therapeutic strategies.

InChI:InChI=1/C14H20N3O9/c1-6(18)22-5-10-11(23-7(2)19)12(24-8(3)20)13(25-9(4)21)14(26-10)16-17-15/h10-15H,5H2,1-4H3/q+1

Upstream product

• 108-24-7 acetic anhydride 
• 85219-64-3 3,4,6-Tri-O-acetyl-β-D-glucopyranosylazid 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 92051-23-5 1,3,4,6-tetra-O-acetyl-2-O-trifluoromethanesulfonyl-β-D-mannopyranose 
• 141607-22-9 diphenyl (tetra-O-acetyl-α-D-glucopyranosyl) phosphate 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 
• 604-69-3 β-D-glucose pentaacetate 
• 3947-62-4 2,3,4,5-tetra-O-acetyl-D-glucopyranose 
• 2280-44-6 D-Glucose 
• 6919-96-6 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 83-87-4 D-glucose pentaacetate 
• 74808-10-9 O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate 
• 20379-59-3 D-glucopyranosyl azide 

Downstream Products

• 73174-37-5 4,6-O-benzylidene-β-D-glucopyranosyl azide 
• 26295-42-1 1’-(4-phenyl-[1,2,3]-triazol-1-yl)-2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranose 
• 20379-60-6 α-D-Glucopyranosyl azide 
• 155919-81-6 2,3,4,6-tetraacetyl-1-β-D-N-glucopyranose 
• 155919-82-7 2,3,4,6-tetraacetyl-1-β-D-N-<(O,O-diethyl-N-bis(2-chloroethyl)amido)phosphimino>glucopyranose 
• 41355-50-4 2,3,4,6-tetra-O-acetyl-D-glucosyl-1-amine 
• 78028-93-0 1-N-(1-benzyl N-(tert-butyloxycarbonyl)-4-aspart-4-oyl)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine 
• 4451-35-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl chloride 
• 94388-46-2 1-N-benzylidene-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)imine 
• 353264-43-4 1-N-(4-methylbenzoyl)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine 
• 18918-50-8 1-N-benzoyl-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine 
• 18918-58-6 1-N-(4-chlorobenzoyl)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine 
• 18918-52-0 1-N-(4-nitrobenzoyl)-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)amine 

Relevant articles and documents

High-Yielding Catalytic Synthesis of Glycosyl Azides from Peracylated Sugars

In the presence of a catalyst generated from SnCl4 and AgClO4, or Yb(OTf)3, various glycosyl azides are synthesized in high yields with complete stereoselectivities from peracylated sugars and trimethylsilyl azide by choosing a suitable solvent such as dichloromethane or nitromethane.

Ex post glycoconjugation of phthalocyanines

Figure presented For the first time, fully fledged phthalocyanines (Pcs) were ex post glycoconjugated, that is, via 1,3-dipolar cycloaddition reaction. This divergent approach gains rapid access to a broad range of highly diverse Pcs bearing chemically sensitive substituents. This will be a breakthrough in generating structure-activity relationships (SAR) for the development of novel bioactive molecules.

Synthesis of new triazole linked carbohybrids with ROS-mediated toxicity in breast cancer

Carbohybrids are an important class of molecules which exhibit diverse biological activities and are present as structural motifs in many natural products. Two series of new triazole linked N-glycosides of coumarins and quinolones (n = 27) were efficiently synthesized starting from 1-azido-2,3,4,6-tetra-O-acetyl β-d-glucose and 1-azido-2,3,4,6-tetra-O-acetyl β-d-galactose reacting with various 4-O-propargyl coumarins and 4-O-propargyl quinolones in shorter reaction time (30 min) under microwave assisted conditions. Anticancer activity of these newly synthesized triazole linked N-glycosides of coumarins and quinolones was determined in detail through cellular assays against MCF-7 (breast cancer cell line), HepG2 (liver cancer cell line), HCT-116 (colon cancer cell line) and Huh-7.5 cell lines. The selected library member displayed low micromolar (IC50 10.97 μM) and selective toxicity against the breast cancer cell line (MCF-7). Mechanistic studies showed that the anticancer activity of the active compound was because of the generation of reactive oxygen species (ROS).

Novel class of non-ionic monocatenary and bolaform alkylglycoside surfactants. Synthesis by microwave-assisted glycosylation and olefin cross-metathesis or by 'click-chemistry': physicochemical studies

We develop herein the synthesis of a new class of monocatenary and bolaform surfactants from d-glucose, d-galactose and lactose. Two main pathways have been investigated: microwave-assisted glycosylation followed by olefin cross-metathesis, and the one-step click-chemistry methodology. Tensioactive properties of these new compounds have been studied in order to characterize the physicochemical behaviour of these new carbohydrate-based compounds in water.

Application of ball milling technology to carbohydrate reactions-II. Solvent-free mechanochemical synthesis of glycosyl azides

Glycosyl azides have been prepared from a range of readily available glycosyl halides by a solvent-free mechanochemical procedure employing a planetary ball mill in good to excellent yields.

Carbohydrate-functionalized N-heterocyclic carbene Ru(ii) complexes: Synthesis, characterization and catalytic transfer hydrogenation activity

Three Ru complexes containing carbohydrate/N-heterocyclic carbene hybrid ligands were synthesized that were comprised of a triazolylidene coordination site and a directly linked per-acetylated glucosyl (5Glc) or galactosyl unit (5Gal), or a glycosyl unit linked through an ethylene spacer (6). Electrochemical and UV-vis analysis indicate only minor perturbation of the electronic configuration of the metal center upon carbohydrate installation. Deprotection of the carbohydrate was accomplished under basic conditions to afford complexes that were stable in solution over several hours, but decomposed in the solid state. Complexes 5 and 6 were used as pre-catalysts for transfer hydrogenation of ketones under basic conditions, i.e. conditions that lead to in situ deprotection of the carbohydrate entity. The carbohydrate directly influences the catalytic activity of the metal center. Remotely linked carbohydrates (complex 6) induce significantly lower catalytic activity than directly linked carbohydrates (complexes 5Glc, 5Gal), while unfunctionalized triazolylidenes are an order of magnitude more active. These observations and substrate variations strongly suggest that substrate bonding is rate-limiting for transfer hydrogenation in these hybrid carbohydrate/triazolylidene systems.

Straightforward synthesis of novel Akt inhibitors based on a glucose scaffold

Glucose-based analogues of phosphatidylinositol 3-phosphate were straightforwardly synthesised from 2,3,4,6-tetra-O-acetyl-D-glucosyl bromide as protein kinase B (PKB/Akt) inhibitors. β-D-Glucuronyl diethyl phosphoramidate was identified as a promising hit through biological screening in two different cellular systems. In addition, RNA interference experiments (siRNA) provide evidence of the ability of the compound to exert biological effects specifically through Akt signalling.

The first synthesis of the N-glucosyl analogue of the antitumor agent etoposide

The first synthesis of 1-aminoglucose analogue of the antitumor agent etoposide is accomplished by condensation of 4,6-tO-ethylidene-2,3-di-tO-trimethylsilyl-β-D-glucopyranosylamine with 4-bromo-4-deoxy-4′-demethylepipodophyllotoxin in the presence of Hg(

Synthesis and comparative study of emulsifying and biological properties of triazolated glucolipids

Glycolipids represent an attractive type of nonionic emulsifiers (surfactants) due to their abundant renewable resources and good biocompatibility. General preparation methods for glycolipids include enzymatic esterification or Lewis acid-catalyzed glycosylation. In this study, we report the synthesis of a novel series of triazolated alkyl glucolipids as emulsifiers by copper(I)-catalyzed click reactions, with side-chain length ranging from 4 to 10 carbons. The surface-active properties, foaming properties, emulsion properties, thermal stability as well as cytotoxicity of the synthesized compounds are evaluated to establish a comprehensive structure-property profiles, and results suggest the potential utility of medium sized glucolipids in, for example, pharmaceutical and food industries as they show superior performance than the tested commercial references.

Phase transfer catalysis as a general and stereoselective entry into glycosyl azides from glycosyl halides

Peracetylated glycosyl- and glycobiosyl bromides and chlorides 1-5 including acetochloroneuraminic acid 6 were converted to their corresponding glycosyl azides 7-12 in 93-98% yields under phase transfer catalyzed conditions. The stereoselective reactions occurred with complete inversion at the anomeric centers to provide a general, high-yielding entry into 1,2-trans-glycosyl azides together with α-sialic acid azide.