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

• ChemBase ID: 145825
• 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-MBJXGIAVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-azidooxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-azidooxan-2-yl]methyl acetate
• Synonyms: 1-Azido-1-deoxy-β-D-galactopyranoside tetraacetate; NSC 272456; 1-Azido-1-deoxy-β-D-glucopyranoside tetraacetate; 1-叠氮-1-脱氧-β-D-吡喃半乳糖苷四乙酸酯; 1-叠氮-1-脱氧-β-D-吡喃葡萄糖苷四乙酸酯

Database IDs

• CAS Number: 13992-25-1; 13992-26-2
• MDL Number: MFCD00181721
• PubChem SID: 162240027; 24873726; 24873728
• PubChem CID: 2781041

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

Physical Property

• Melting Point: 127-131 °C(lit.); 96-99 °C(lit.)
• Optical Rotation: [α]/D -29°, c = 1% in H2O; [α]/D -30°, c = 1% in chloroform; [α]25/D -15°, c = 1 in chloroform

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: 97%
• Empirical Formula (Hill Notation): C14H19N3O9

DETAILS

Sigma Aldrich - 513970

Packaging
1 g in glass bottle

Sigma Aldrich - 513997

Packaging
1 g in glass bottle
Application
Reactant for:
• Synthesis of Protein Tyrosine Phosphatase 1B inhibitor1
• Synthesis of glycoconjugate carbonic anhydrase inhibitors by ruthenium-catalyzed azide-alkyne 1,3-dipolar cycloaddition2
• Synthesis of variously coupled conjugates of D-glucose via click chemistry for inhibition of glycogen phosphorylase3
• Hydrogenation reactions4
• Preparation of posttranslationally modified peptides efficiently mimicking neoantigens in relation to autoimmune disease5