2-{[(2S,4aR,6S,7R,8R,8aS)-6-(benzyloxy)-7-acetamido-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-8-yl]oxy}acetic acid

• ChemBase ID: 161330
• Molecular Formular: C24H27NO8
• Molecular Mass: 457.47308
• Monoisotopic Mass: 457.17366683
• SMILES: [C@H]12[C@@H]([C@@H]([C@H](O[C@@H]1CO[C@@H](O2)c1ccccc1)OCc1ccccc1)NC(=O)C)OCC(=O)O
• Canonical SMILES: OC(=O)CO[C@H]1[C@@H]2O[C@H](OC[C@H]2O[C@@H]([C@H]1NC(=O)C)OCc1ccccc1)c1ccccc1
• InChI: InChI=1S/C24H27NO8/c1-15(26)25-20-22(29-14-19(27)28)21-18(13-31-23(33-21)17-10-6-3-7-11-17)32-24(20)30-12-16-8-4-2-5-9-16/h2-11,18,20-24H,12-14H2,1H3,(H,25,26)(H,27,28)/t18-,20-,21-,22-,23+,24+/m1/s1
• InChIKey: KBBGPRDVHUWBLB-UBTSVQAUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[(2S,4aR,6S,7R,8R,8aS)-6-(benzyloxy)-7-acetamido-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-8-yl]oxy}acetic acid
• IUPAC Traditional name: {[(2S,4aR,6S,7R,8R,8aS)-6-(benzyloxy)-7-acetamido-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-8-yl]oxy}acetic acid
• Synonyms: Benzyl 2-Acetamido-4,6-O-Benzylidene-3-Carboxymethyl-2-Deoxy-α-D-Glucopyranoside; Benzyl N-Acetyl-4,6-O-benzylidene Normuranic Acid; N-Acetyl-1-O-(phenylmethyl)-4,6-O-(phenylmethylene)-α-normuramic Acid

Database IDs

• CAS Number: 14595-22-3
• PubChem SID: 162255465
• PubChem CID: 11891372

CALCULATED PROPERTIES

• Acid pKa: 3.4939895
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 0.4357419
• LogD (pH = 7.4): -0.9439669
• Log P: 2.4332142
• Molar Refractivity: 114.1079 cm^3
• Polarizability: 45.822163 Å^3
• Polar Surface Area: 112.55 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Wjite Solid
• Melting Point: 220-222°C