[(2R,3S,4R,5R,6R)-3,4-bis(acetyloxy)-6-amino-5-acetamidooxan-2-yl]methyl acetate

• ChemBase ID: 158920
• Molecular Formular: C14H22N2O8
• Molecular Mass: 346.33308
• Monoisotopic Mass: 346.13761567
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)N)NC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@@H]1[C@H](COC(=O)C)O[C@H]([C@H]([C@H]1OC(=O)C)NC(=O)C)N
• InChI: InChI=1S/C14H22N2O8/c1-6(17)16-11-13(23-9(4)20)12(22-8(3)19)10(24-14(11)15)5-21-7(2)18/h10-14H,5,15H2,1-4H3,(H,16,17)/t10-,11-,12-,13-,14-/m1/s1
• InChIKey: DKGKXBJJPLBTOQ-DHGKCCLASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R,6R)-3,4-bis(acetyloxy)-6-amino-5-acetamidooxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4R,5R,6R)-3,4-bis(acetyloxy)-6-amino-5-acetamidooxan-2-yl]methyl acetate
• Synonyms: 2-(Acetylamino)-2-deoxy-β-D-glucopyranosylamine 3,4,6-Triacetate; 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine

Database IDs

• CAS Number: 4515-24-6
• PubChem SID: 162253055
• PubChem CID: 10893359

CALCULATED PROPERTIES

• Acid pKa: 12.539964
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -4.283009
• LogD (pH = 7.4): -2.5927944
• Log P: -2.00408
• Molar Refractivity: 76.1367 cm^3
• Polarizability: 31.787416 Å^3
• Polar Surface Area: 143.25 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: Pale Yellow Solid
• Melting Point: 247-249°C (dec.)

REFERENCES

• Harrison, A., et al.: Bioorg. Med. Chem., 2, 1339 (1994)