[(2R,3R,4S,5S,6S)-3,4,5-tris(acetyloxy)-6-azidooxan-2-yl]methyl acetate

• ChemBase ID: 154147
• Molecular Formular: C14H19N3O9
• Molecular Mass: 373.31536
• Monoisotopic Mass: 373.1121292
• SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@@H]([C@H](O1)N=[N+]=[N-])OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: [N-]=[N+]=N[C@H]1O[C@H](COC(=O)C)[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: 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-DGTMBMJNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5S,6S)-3,4,5-tris(acetyloxy)-6-azidooxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4S,5S,6S)-3,4,5-tris(acetyloxy)-6-azidooxan-2-yl]methyl acetate
• Synonyms: 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl azide; α-D-Mannopyranosyl azide tetraacetate

Database IDs

• MDL Number: MFCD05664724
• PubChem SID: 162248286
• PubChem CID: 12953526

CALCULATED PROPERTIES

• Acid pKa: 14.3627205
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): -0.4617388
• LogD (pH = 7.4): -0.46173885
• Log P: -0.34769315
• Molar Refractivity: 78.8219 cm^3
• Polarizability: 32.2624 Å^3
• Polar Surface Area: 143.86 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (TLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C14H19N3O9

DETAILS

Sigma Aldrich - G4168

Application
Used to make N-linked glycopeptides in glycobiology.
α-D-Mannopyranosyl azide tetraacetate is used to make N-linked glycopeptides in glycobiology and in "click" chemistry. 1