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

• ChemBase ID: 178061
• Molecular Formular: C14H22ClNO9
• Molecular Mass: 383.77878
• Monoisotopic Mass: 383.09830897
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H](O[C@H]1COC(=O)C)OC(=O)C)N)OC(=O)C)OC(=O)C.Cl
• Canonical SMILES: CC(=O)OC[C@@H]1O[C@H](OC(=O)C)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)N.Cl
• InChI: InChI=1S/C14H21NO9.ClH/c1-6(16)20-5-10-12(21-7(2)17)13(22-8(3)18)11(15)14(24-10)23-9(4)19;/h10-14H,5,15H2,1-4H3;1H/t10-,11-,12-,13-,14+;/m1./s1
• InChIKey: BQLUYAHMYOLHBX-XHNNQSHGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R,6R)-3,4,6-tris(acetyloxy)-5-aminooxan-2-yl]methyl acetate hydrochloride
• IUPAC Traditional name: [(2R,3S,4R,5R,6R)-3,4,6-tris(acetyloxy)-5-aminooxan-2-yl]methyl acetate hydrochloride
• Synonyms: 1-Thio-α-D-galactopyranose Pentaacetate; 2,3,4,6-Tetra-O-acetyl-1-S-acetyl-1-thio-α-D-galactopyranoside

Database IDs

• CAS Number: 130796-15-5
• PubChem SID: 164233971
• PubChem CID: 57373440

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -3.5694783
• LogD (pH = 7.4): -1.8778528
• Log P: -1.2749194
• Molar Refractivity: 74.1869 cm^3
• Polarizability: 31.383043 Å^3
• Polar Surface Area: 140.45 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Ether; Ethyl Acetate
• Apperance: White Powder
• Melting Point: 95°C

DETAILS

Toronto Research Chemicals - T225000

Used in the synthesis and evaluation for iNKT stimulation of α-S-galactosylceramide.

REFERENCES

• Kawano, T., et al.: Science, 278, 1626 (1997)
• Wang, B., et al.: J. Exp. Med., 194, 313 (1997)
• Hansen, D., et al.: Eur. J. Immunol., 33, 2588 (1997)
• Forestier, C., et al.: J. Immunol., 178, 1415 (1997)