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

• ChemBase ID: 143318
• Molecular Formular: C14H22ClNO9
• Molecular Mass: 383.77878
• Monoisotopic Mass: 383.09830897
• SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)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-XAWYEFCRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R,6S)-3,4,6-tris(acetyloxy)-5-aminooxan-2-yl]methyl acetate hydrochloride
• IUPAC Traditional name: [(2R,3S,4R,5R,6S)-3,4,6-tris(acetyloxy)-5-aminooxan-2-yl]methyl acetate hydrochloride
• Synonyms: 1,3,4,6-Tetra-O-acetyl-β-D-glucosamine; 2-Amino-2-deoxy-β-D-glucopyranose 1,3,4,6-tetraacetate; 1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-β-D-glucopyranose hydrochloride; 2-Amino-2-deoxy-α-D-glucopyranose 1,3,4,6-Tetraacetate Hydrochloride; 1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-α-D-glucopyranose Hydrochloride

Database IDs

• CAS Number: 10034-19-2; 10034-20-5
• MDL Number: MFCD01075204
• PubChem SID: 162237539
• PubChem CID: 202259

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: DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: 174-181°C (dec.)
• Optical Rotation: [α]/D 30.0±2.0°, c = 1 in H2O

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3

Product Information

• Purity: ≥98% (HPLC)
• Compostion: carbon, 42.9-44.7%; nitrogen, 3.4-3.9%
• Empirical Formula (Hill Notation): C14H21NO9 · HCl

DETAILS

Sigma Aldrich - 728314

Packaging
1 g in glass bottle

Toronto Research Chemicals - T237495

A potential metabolic inhibitor of cellular-membrane glycoconjugates.

REFERENCES

• Mark, B., et al.: J. Biol. Chem., 276, 10330 (2001)
• Maier, T., et al.: J. Mol. Biol., 328, 669 (2001)
• Anon, et al.: Bioorg. Med. Chem., 12, 6473 (2001)
• Tropak, M., et al.: J. Biol. Chem., 279, 13478 (2001)