N-[(2R,3R,4R,5S,6R)-2-azido-4-hydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide

• ChemBase ID: 159122
• Molecular Formular: C14H24N4O10
• Molecular Mass: 408.36116
• Monoisotopic Mass: 408.14924299
• SMILES: C(=O)(C)N[C@H]1[C@@H](O[C@@H]([C@H]([C@@H]1O)O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)CO)N=[N+]=[N-]
• Canonical SMILES: OC[C@H]1O[C@@H](N=[N+]=[N-])[C@@H]([C@H]([C@@H]1O[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O)O)NC(=O)C
• InChI: InChI=1S/C14H24N4O10/c1-4(21)16-7-9(23)12(6(3-20)26-13(7)17-18-15)28-14-11(25)10(24)8(22)5(2-19)27-14/h5-14,19-20,22-25H,2-3H2,1H3,(H,16,21)/t5-,6-,7-,8+,9-,10+,11-,12-,13-,14+/m1/s1
• InChIKey: CYVRAOFCZKOGIO-LODBTCKLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4R,5S,6R)-2-azido-4-hydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2R,3R,4R,5S,6R)-2-azido-4-hydroxy-6-(hydroxymethyl)-5-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
• Synonyms: Galβ1-4GlcNAc Azide; -(Acetylamino)-2-deoxy-4-O-β-D-galactopyranosyl-β-D-glucopyranosyl Azide; 2-(Acetylamino)-2-deoxy-4-O-(β-D-galactopyranosyl)-β-D-glucopyranosyl Azide

Database IDs

• CAS Number: 187988-46-1
• PubChem SID: 162253257
• PubChem CID: 71312815

CALCULATED PROPERTIES

• Acid pKa: 11.9279
• H Acceptors: 12
• H Donor: 7
• LogD (pH = 5.5): -4.2851114
• LogD (pH = 7.4): -4.2851233
• Log P: -4.171066
• Molar Refractivity: 85.7305 cm^3
• Polarizability: 34.912895 Å^3
• Polar Surface Area: 207.6 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A168225

β-gylcosyl azide derivative used in the preparation of biantennary N-linked glycoform of CD52.

REFERENCES

• Pratt, M.R. et al.: J. Am. Chem. Soc., 125, 6149 (2003)