513997

1-Azido-1-desoxy-β-D-glucopyranosidtetraacetat

• Synonym(e): NSC 272456
• Empirische Formel (Hill-System): C₁₄H₁₉N₃O₉
• CAS-Nummer: 13992-25-1
• Molekulargewicht: 373.32
• MDL-Nummer: MFCD00181721
• UNSPSC-Code: 12352200
• PubChem Substanz-ID: 24873728
• NACRES: NA.22

Eigenschaften

• Form: solid
• Optische Aktivität: [α]/D -29°, c = 1% in H₂O; [α]/D -30°, c = 1% in chloroform
• Eignung der Reaktion: reaction type: click chemistry
• mp (Schmelzpunkt): 127-131 °C (lit.)
• SMILES String: CC(=O)OC[C@H]1O[C@@H](N=[N+]=[N-])[C@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]1OC(C)=O
• InChI: 1S/C14H19N3O9/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/h10-14H,5H2,1-4H3/t10-,11+,12+,13-,14-/m1/s1
• InChIKey: NHNYHKRWHCWHAJ-MBJXGIAVSA-N

Beschreibung

Anwendung

1-Azido-1-deoxy-β-D-glucopyranoside tetraacetate can be used as a reactant to synthesize:

• 1,2,3-Triazole-boron dipyrromethenes (BODIPYs) containing glucose groups via Cu(I)-catalyzed azide–alkyne ″click″ cycloaddition reaction conditions.
• 1-(β-D-glycosyl)-5-benzenesulfonamide-1,2,3-triazole derivatives by ruthenium-catalyzed azide-alkyne cycloaddition reactions.
• 2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosylamine by palladium catalyzed hydrogenation reaction.
• Glycoside annulated dihydropyrimidinone derivatives by one-pot five-component condensation reaction with tert-butyl β-ketoester, arylaldehyde, urea and propargyl alcohol.

Reactant for:

• Synthesis of Protein Tyrosine Phosphatase 1B inhibitor
• Synthesis of glycoconjugate carbonic anhydrase inhibitors by ruthenium-catalyzed azide-alkyne 1,3-dipolar cycloaddition
• Synthesis of variously coupled conjugates of D-glucose via click chemistry for inhibition of glycogen phosphorylase
• Hydrogenation reactions
• Preparation of posttranslationally modified peptides efficiently mimicking neoantigens in relation to autoimmune disease

Sicherheitshinweise

• Lagerklassenschlüssel: 11 - Combustible Solids
• WGK: WGK 3
• Flammpunkt (°F): Not applicable
• Flammpunkt (°C): Not applicable
• Persönliche Schutzausrüstung: Eyeshields, Gloves, type N95 (US)