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

• ChemBase ID: 169663
• Molecular Formular: C16H23NO10
• Molecular Mass: 389.35452
• Monoisotopic Mass: 389.13219594
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H](O[C@H]1COC(=O)C)OC(=O)C)NC(=O)C)OC(=O)C)OC(=O)C
• 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)NC(=O)C
• InChI: InChI=1S/C16H23NO10/c1-7(18)17-13-15(25-10(4)21)14(24-9(3)20)12(6-23-8(2)19)27-16(13)26-11(5)22/h12-16H,6H2,1-5H3,(H,17,18)/t12-,13-,14-,15-,16+/m1/s1
• InChIKey: OVPIZHVSWNOZMN-QCODTGAPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R,6R)-3,4,6-tris(acetyloxy)-5-acetamidooxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4R,5R,6R)-3,4,6-tris(acetyloxy)-5-acetamidooxan-2-yl]methyl acetate
• Synonyms: 2-(Acetylamino)-2-deoxy-α-D-glucopyranose 1,3,4,6-Tetraacetate; 1,3,4,6-Tetra-O-acetyl-2-acetamido-2-deoxy-α-D-glucopyranose; N-Acetyl-α-D-glucosamine Tetraacetate; NSC 231931; α-D-Glucosamine Pentaacetate

Database IDs

• CAS Number: 7784-54-5
• PubChem SID: 162263795
• PubChem CID: 99515

CALCULATED PROPERTIES

• Acid pKa: 12.145199
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -1.456073
• LogD (pH = 7.4): -1.4560797
• Log P: -1.4560728
• Molar Refractivity: 83.6307 cm^3
• Polarizability: 34.8191 Å^3
• Polar Surface Area: 143.53 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Water
• Apperance: White SolidOff-White Solid
• Melting Point: 127-130°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - G515001

A proteted form of glucosamine

REFERENCES

• Cudic, P., et al.: Bioorg. Med. Chem. Lett., 11, 3107 (2001)