1-Azido-1-deoxy-β-D-glucopyranoside tetraacetate

Synonyms (s): NSC 272456

Empirical Formula (Hill Notation): C₁₄H₁₉N₃O₉

Size: 1 g

Product Introduction

Molecular Weight	373.32
NACRES	NA.22
CAS Number	13992-25-1
MDL Number	MFCD00181721
PubChem Substance ID	24873728
Form	Solid
Reaction Suitability	Reaction type: click chemistry
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
InChI key	NHNYHKRWHCWHAJ-MBJXGIAVSA-N

Application

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 inhibitorSynthesis of glycoconjugate carbonic anhydrase inhibitors by ruthenium-catalyzed azide-alkyne 1,3-dipolar cycloadditionSynthesis of variously coupled conjugates of D-glucose via click chemistry for inhibition of glycogen phosphorylaseHydrogenation reactionsPreparation of posttranslationally modified peptides efficiently mimicking neoantigens in relation to autoimmune disease

Safety Information

Storage Class Code	13 - Non Combustible Solids
WGK	WGK 3

For research use only. Not for clinical use.