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

• ChemBase ID: 158896
• Molecular Formular: C16H22N2O10
• Molecular Mass: 402.35328
• Monoisotopic Mass: 402.12744491
• SMILES: [C@@H]1([C@@H]([C@@H](/C(=N\OC(=O)C)/O[C@H]1COC(=O)C)NC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)OC[C@@H]1O/C(=N/OC(=O)C)/[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)NC(=O)C
• InChI: InChI=1S/C16H22N2O10/c1-7(19)17-13-15(26-10(4)22)14(25-9(3)21)12(6-24-8(2)20)27-16(13)18-28-11(5)23/h12-15H,6H2,1-5H3,(H,17,19)/b18-16+/t12-,13-,14-,15-/m1/s1
• InChIKey: PMNZTSIWBRXCQW-HFOXSZHISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(3R,4R,5S,6R)-4,5-bis(acetyloxy)-6-[(acetyloxy)methyl]-3-acetamidooxan-2-ylidene]amino acetate
• IUPAC Traditional name: [(3R,4R,5S,6R)-4,5-bis(acetyloxy)-6-[(acetyloxy)methyl]-3-acetamidooxan-2-ylidene]amino acetate
• Synonyms: 2-(Acetylamino)-N-(acetyloxy)-2-deoxy-D-gluconimidic Acid δ-Lactone 3,4,6-Triacetate; LogNAc-tetraacetate; 2-Acetamido-2-deoxy-D-gluconhydroximo-1,5-lactone 1,3,4,6-tetraacetate

Database IDs

• CAS Number: 132152-77-3
• PubChem SID: 162253031
• PubChem CID: 29970219

CALCULATED PROPERTIES

• Acid pKa: 11.801185
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): -1.5906265
• LogD (pH = 7.4): -1.5906414
• Log P: -1.5906261
• Molar Refractivity: 86.5767 cm^3
• Polarizability: 35.58474 Å^3
• Polar Surface Area: 155.89 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: White Foam

DETAILS

Toronto Research Chemicals - A155250

An intermediate in the synthesis of PugNAc (Cat. No. A15725), an inhibitor of glucosamidase.

REFERENCES

• Beer, D., et al.: Helv. Chim. Acta., 73, 1918 (1990)
• Horsch, M., et al.: Eur. J. Biochem., 197, 815 (1990)
• Horsch, M., et al.: J. Enzyme Inhib., 7, 47 (1990)
• Horsch, M., et al.: Eur. J. Biochem., 237, 476 (1990)