N-[(4aR,7R,8R,8aS)-8-hydroxy-6-(hydroxyimino)-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl]acetamide

• ChemBase ID: 158864
• Molecular Formular: C15H18N2O6
• Molecular Mass: 322.31322
• Monoisotopic Mass: 322.11648631
• SMILES: O1/C(=N\O)/[C@H]([C@H]([C@H]2[C@H]1COC(O2)c1ccccc1)O)NC(=O)C
• Canonical SMILES: O/N=C/1\O[C@@H]2COC(O[C@H]2[C@@H]([C@@H]1NC(=O)C)O)c1ccccc1
• InChI: InChI=1S/C15H18N2O6/c1-8(18)16-11-12(19)13-10(22-14(11)17-20)7-21-15(23-13)9-5-3-2-4-6-9/h2-6,10-13,15,19-20H,7H2,1H3,(H,16,18)/b17-14-/t10-,11-,12-,13-,15?/m1/s1
• InChIKey: PIYCZWMJRKZNLW-CVMSKJGUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(4aR,7R,8R,8aS)-8-hydroxy-6-(hydroxyimino)-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• IUPAC Traditional name: N-[(4aR,7R,8R,8aS)-8-hydroxy-6-(hydroxyimino)-2-phenyl-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
• Synonyms: 2-(Acetylamino)-2-deoxy-N-hydroxy-4,6-O-[(R)-phenylmethylene]-D-gluconimidic Acid δ-Lactone; 2-Acetamido-4,6-O-benzylidene-2-deoxy-D-gluconohydroximo-1,5-lactone

Database IDs

• CAS Number: 132063-03-7
• PubChem SID: 162252999
• PubChem CID: 71312719

CALCULATED PROPERTIES

• Acid pKa: 9.199104
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 0.108097464
• LogD (pH = 7.4): 0.10137104
• Log P: 0.108183995
• Molar Refractivity: 76.8543 cm^3
• Polarizability: 30.894844 Å^3
• Polar Surface Area: 109.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 229-231°C

DETAILS

Toronto Research Chemicals - A142425

2-Acetamido-4,6-O-benzylidene-2-deoxy-D-gluconohydroximo-1,5-lactone is used in synthesis of 2-acetamido-2-deoxy-D-gluconohydroximolactone (PUGNAc), a strong inhibitor of β-N-acetylglucosaminidases.

REFERENCES

• Horsch, M., et al.: Eur. J. Biochem., 197, 815 (1991)
• Horsch, M., et al.: Eur. J. Biochem., 237, 476 91996), Fernandes, M., et al.: J. Biol. Chem., 272, 814 (1991)