[(2R,3S,4R,5R,6Z)-3,4-bis(acetyloxy)-5-acetamido-6-{[(phenylcarbamoyl)oxy]imino}oxan-2-yl]methyl acetate

• ChemBase ID: 158941
• Molecular Formular: C21H25N3O10
• Molecular Mass: 479.4373
• Monoisotopic Mass: 479.15399402
• SMILES: [C@@H]1([C@@H]([C@@H](/C(=N/OC(=O)Nc2ccccc2)/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)Nc2ccccc2)/[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)NC(=O)C
• InChI: InChI=1S/C21H25N3O10/c1-11(25)22-17-19(32-14(4)28)18(31-13(3)27)16(10-30-12(2)26)33-20(17)24-34-21(29)23-15-8-6-5-7-9-15/h5-9,16-19H,10H2,1-4H3,(H,22,25)(H,23,29)/b24-20-/t16-,17-,18-,19-/m1/s1
• InChIKey: WIPJJKKTCDJFST-CQPCARDBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R,6Z)-3,4-bis(acetyloxy)-5-acetamido-6-{[(phenylcarbamoyl)oxy]imino}oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4R,5R,6Z)-3,4-bis(acetyloxy)-5-acetamido-6-{[(phenylcarbamoyl)oxy]imino}oxan-2-yl]methyl acetate
• Synonyms: 2-(Acetylamino)-2-deoxy-N-[[(phenylamino)carbonyl]oxy]-D-gluconimidic Acid δ-Lactone 3,4,6-Triacetate; O-(2-Acetamido-3,4,6-tri-O-acetyl-D-glucopyranosylidene)amino N-phenyl Carbamate (E/Z Mixture)

Database IDs

• CAS Number: 132063-04-8
• PubChem SID: 162253076
• PubChem CID: 56845650

CALCULATED PROPERTIES

• Acid pKa: 11.710882
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 0.3170725
• LogD (pH = 7.4): 0.3170538
• Log P: 0.3170729
• Molar Refractivity: 111.7085 cm^3
• Polarizability: 44.34388 Å^3
• Polar Surface Area: 167.92 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Ethanol; Ethyl Acetate; Methanol
• Apperance: White Foam

DETAILS

Toronto Research Chemicals - A161195

Intermediate in the preparation of 2-Acetamido-2-deoxy-D-gluconohydroximolactone (PUGNAc).

REFERENCES

• Stubbs, K., et al.: Org. Biomol. Chem., 4, 839 (2006)