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

• ChemBase ID: 178191
• Molecular Formular: C14H20O9
• Molecular Mass: 332.3032
• Monoisotopic Mass: 332.11073222
• SMILES: [C@@H]1([C@@H]([C@@H](CO[C@H]1COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)OC[C@@H]1OC[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C14H20O9/c1-7(15)19-5-11-13(22-9(3)17)14(23-10(4)18)12(6-20-11)21-8(2)16/h11-14H,5-6H2,1-4H3/t11-,12-,13-,14-/m1/s1
• InChIKey: ULWHEXUWXLOVPV-AAVRWANBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4R,5R)-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4R,5R)-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate
• Synonyms: 2-Amino-2-deoxy-β-D-glucopyranose 1,3,4,6-Tetraacetate Hydrochloride; NSC 82044; 1,3,4,6-Tetra-O-acetyl-2-amino-2-deoxy-β-D-glucopyranose Hydrochloride

Database IDs

• CAS Number: 10034-20-5
• PubChem SID: 164234101
• PubChem CID: 10506743

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.80381364
• LogD (pH = 7.4): -0.80381364
• Log P: -0.80381364
• Molar Refractivity: 71.4995 cm^3
• Polarizability: 29.858467 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 197-200°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T237500

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)