935417

β-D-Glucopyranosyl azide

≥95%

• Synonym(s): 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl azide, 2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide, Glucopyranosyl azide, 2-acetamido-2-deoxy-, 3,4,6-triacetate, β-D-, Glucopyranosyl azide, 2-acetamido-2-deoxy-, triacetate
• Empirical Formula (Hill Notation): C₁₄H₂₀N₄O₈
• CAS Number: 6205-69-2
• Molecular Weight: 372.33
• MDL number: MFCD00216968
• UNSPSC Code: 12352100
• NACRES: NA.21

Properties

• Quality Level: 100
• Assay: ≥95%
• form: powder or crystals
• color: white to light yellow
• bp: 501.81 °C
• mp: 128-130 °C
• density: 1.30 g/mL
• storage temp.: −20°C
• SMILES string: [N-]=[N+]=NC1OC(COC(=O)C)C(OC(=O)C)C(OC(=O)C)C1NC(=O)C
• InChI: InChI=1S/C14H20N4O8/c1-6(19)16-11-13(25-9(4)22)12(24-8(3)21)10(5-23-7(2)20)26-14(11)17-18-15/h10-14H,5H2,1-4H3,(H,16,19)/t10-,11-,12-,13-,14-/m1/s1
• InChI key: RMCFMPMNMQZHSF-DHGKCCLASA-N

Description

Application

β-D-Glucopyranosyl azide, 2-(acetylamino)-2-deoxy-, 3,4,6-triacetate is commonly used in organic synthesis, particularly for the preparation of glycosyl azides, which are versatile intermediates in the synthesis of glycoconjugates. In carbohydrate chemistry, it can be employed for modifying and functionalizing carbohydrates, including the introduction of azide groups. These azide-modified carbohydrates can participate in click chemistry reactions, enabling the development of bioconjugates and glycoarrays. In drug discovery, this compound aids in the design and synthesis of carbohydrate-based therapeutics, such as glycosidase inhibitors or glycoconjugate vaccines, by modifying carbohydrate structures. For biochemical research, this compound is valuable in studying carbohydrate-protein interactions, glycan biosynthesis, and glycoprotein engineering. It allows for the modification and labeling of carbohydrates for subsequent biological assays and analyses. Finally, as an azide derivative, it finds application in click chemistry reactions, specifically the azide-alkyne cycloaddition reaction (commonly known as the "click reaction"). This reaction enables efficient and selective labeling, bioconjugation, and cross-linking in various biological and materials science applications.

Features and Benefits

β-D-Glucopyranosyl azide, 2-(acetylamino)-2-deoxy-, 3,4,6-triacetate is a complex carbohydrate and the glycosylation product of 2,3,4,6-tetraacetyl α--D--glucose and 2,3,6 -tri--O--acetyl--2--deoxy--β--D--glucopyranose. This compound has been modified by Click Chemistry with 4-(dimethylamino)pyridine (DMAP). The modification has produced an acetamido group at the C2 position of the glucopyranoside moiety. The compound is available in high purity for research purposes.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable