[(2R,3R,4S,5R,6R)-4,5-bis(acetyloxy)-6-azido-3-{[(2S,3R,4S,5S,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}oxan-2-yl]methyl acetate

• ChemBase ID: 154214
• Molecular Formular: C26H35N3O17
• Molecular Mass: 661.566
• Monoisotopic Mass: 661.19664668
• 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)O[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)COC(=O)C)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)O[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/C26H35N3O17/c1-10(30)37-8-17-20(21(40-13(4)33)23(42-15(6)35)25(44-17)28-29-27)46-26-24(43-16(7)36)22(41-14(5)34)19(39-12(3)32)18(45-26)9-38-11(2)31/h17-26H,8-9H2,1-7H3/t17-,18-,19+,20-,21+,22+,23-,24-,25-,26+/m1/s1
• InChIKey: JFCQZWVIHHPJTD-LTSQYKSLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5R,6R)-4,5-bis(acetyloxy)-6-azido-3-{[(2S,3R,4S,5S,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4S,5R,6R)-4,5-bis(acetyloxy)-6-azido-3-{[(2S,3R,4S,5S,6R)-3,4,5-tris(acetyloxy)-6-[(acetyloxy)methyl]oxan-2-yl]oxy}oxan-2-yl]methyl acetate
• Synonyms: β-Lactosyl azide heptaacetate; 2,3,6-Tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranosyl azide; Hepta-O-acetyl-β-lactosyl azide

Database IDs

• MDL Number: MFCD05664728
• PubChem SID: 162248353
• PubChem CID: 10908490

CALCULATED PROPERTIES

• Acid pKa: 14.363254
• H Acceptors: 12
• H Donor: 0
• LogD (pH = 5.5): -0.9091982
• LogD (pH = 7.4): -0.9091983
• Log P: -0.79515254
• Molar Refractivity: 138.6897 cm^3
• Polarizability: 57.636086 Å^3
• Polar Surface Area: 241.22 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

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): C26H35N3O17

DETAILS

Sigma Aldrich - L3415

Application
Used to synthesize N-linked glycopeptides.