N-[(2S,3R,4R,5S,6R)-2-(benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 131612
• Molecular Formular: C15H21NO6
• Molecular Mass: 311.33034
• Monoisotopic Mass: 311.1368874
• SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@@H]1OCc1ccccc1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H](OCc2ccccc2)[C@@H]([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C15H21NO6/c1-9(18)16-12-14(20)13(19)11(7-17)22-15(12)21-8-10-5-3-2-4-6-10/h2-6,11-15,17,19-20H,7-8H2,1H3,(H,16,18)/t11-,12-,13-,14-,15+/m1/s1
• InChIKey: SKOZFDIGKDPQBO-RYPNDVFKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-2-(benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5S,6R)-2-(benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: α-D-GlcNAc-1→OCH2Ph; Benzyl N-acetyl-α-D-glucosaminide; Benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside; Phenylmethyl 2-(Acetylamino)-2-deoxy-α-D-glucopyranoside; Benzyl 2-Acetamido-2-deoxy-α-D-glucopyranoside

Database IDs

• CAS Number: 13343-62-9
• MDL Number: MFCD00070371
• PubChem SID: 162225889
• PubChem CID: 2801971

CALCULATED PROPERTIES

• Acid pKa: 12.357337
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -0.8529751
• LogD (pH = 7.4): -0.8529792
• Log P: -0.8529748
• Molar Refractivity: 76.3885 cm^3
• Polarizability: 30.718012 Å^3
• Polar Surface Area: 108.25 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: 183-185°C

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3

Product Information

• Classification: Rare Derivatives of Natural Compounds

REFERENCES

• Garcia-Alvarez, I., et al.: J. Med. Chem., 50, 364 (2007)
• McGuigan, C., et al.: J. Med. Chem., 51, 5807 (2007)