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CAS 80321-89-7

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1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-beta-D-glucopyranose

Description:
1,3,4,6-Tetra-O-acetyl-2-azido-2-deoxy-beta-D-glucopyranose is a modified sugar derivative, specifically an azido sugar, which is a key intermediate in carbohydrate chemistry and biochemistry. This compound features a glucopyranose ring structure with four acetyl groups attached to the hydroxyl groups at positions 1, 3, 4, and 6, enhancing its stability and solubility. The azido group at position 2 introduces a reactive functional group that can participate in various chemical reactions, making it useful in synthetic organic chemistry, particularly in the synthesis of glycosylated compounds and in bioconjugation applications. The presence of the acetyl groups also allows for easy deprotection under mild conditions, facilitating further modifications. This compound is typically white to off-white in appearance and is soluble in organic solvents. Its unique structure and reactivity make it valuable in the development of glycosylation reactions and in the study of carbohydrate-related biological processes.
Formula:C14H19N3O9
InChI:InChI=1/C14H19N3O9/c1-6(18)22-5-10-12(23-7(2)19)13(24-8(3)20)11(16-17-15)14(26-10)25-9(4)21/h10-14H,5H2,1-4H3/t10-,11-,12-,13-,14-/m1/s1
SMILES:CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@H](OC(=O)C)O1)N=[N+]=[NH-])OC(=O)C)OC(=O)C
Synonyms:
  • beta-D-glucopyranose, 2-azido-2-deoxy-, 1,3,4,6-tetraacetate
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