[(2R,3R,4R,5R,6R)-3,4-bis(acetyloxy)-5-azido-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxan-2-yl]methyl acetate

• ChemBase ID: 174494
• Molecular Formular: C22H23N3O10
• Molecular Mass: 489.43212
• Monoisotopic Mass: 489.13834395
• SMILES: c1(ccc2c(c1)oc(=O)cc2C)O[C@H]1O[C@H]([C@@H]([C@@H]([C@@H]1N=[N+]=[N-])OC(=O)C)OC(=O)C)COC(=O)C
• Canonical SMILES: [N-]=[N+]=N[C@@H]1[C@@H](Oc2ccc3c(c2)oc(=O)cc3C)O[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)COC(=O)C
• InChI: InChI=1S/C22H23N3O10/c1-10-7-18(29)34-16-8-14(5-6-15(10)16)33-22-19(24-25-23)21(32-13(4)28)20(31-12(3)27)17(35-22)9-30-11(2)26/h5-8,17,19-22H,9H2,1-4H3/t17-,19-,20+,21-,22+/m1/s1
• InChIKey: NUCMFNFBECGZSA-VOFPXKNKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5R,6R)-3,4-bis(acetyloxy)-5-azido-6-[(4-methyl-2-oxo-2H-chromen-7-yl)oxy]oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4R,5R,6R)-3,4-bis(acetyloxy)-5-azido-6-[(4-methyl-2-oxochromen-7-yl)oxy]oxan-2-yl]methyl acetate
• Synonyms: 4-Methyl-7-[(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)oxy]-2H-1-benzopyran-2-one; 4-Methylumbelliferyl 3,4,6-tri-O-Acetyl-2-azido-2-deoxy-α-D-galactopyranoside

Database IDs

• CAS Number: 124167-43-7
• PubChem SID: 164230404
• PubChem CID: 42605333

CALCULATED PROPERTIES

• Acid pKa: 12.5602255
• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): 1.5407958
• LogD (pH = 7.4): 1.5407928
• Log P: 1.6548414
• Molar Refractivity: 113.7029 cm^3
• Polarizability: 45.134644 Å^3
• Polar Surface Area: 153.09 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Pale Yellow Syrup

DETAILS

Toronto Research Chemicals - M334230

Used in the synthesis of 4-methylumbelliferyl glycosides for the detection of α- and β-D-galactopyranosaminidases.

REFERENCES

• Szweda, R. et. al: Can. J. Chem. 67, 1388 (1989)