N-[(3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-oxooxan-3-yl]acetamide

• ChemBase ID: 158942
• Molecular Formular: C29H31NO6
• Molecular Mass: 489.55954
• Monoisotopic Mass: 489.21513772
• SMILES: C1(=O)O[C@H]([C@H]([C@@H]([C@@H]1NC(=O)C)OCc1ccccc1)OCc1ccccc1)COCc1ccccc1
• Canonical SMILES: CC(=O)N[C@@H]1C(=O)O[C@H]([C@H]([C@@H]1OCc1ccccc1)OCc1ccccc1)COCc1ccccc1
• InChI: InChI=1S/C29H31NO6/c1-21(31)30-26-28(35-19-24-15-9-4-10-16-24)27(34-18-23-13-7-3-8-14-23)25(36-29(26)32)20-33-17-22-11-5-2-6-12-22/h2-16,25-28H,17-20H2,1H3,(H,30,31)/t25-,26-,27-,28-/m1/s1
• InChIKey: AYYVTZOWKSEYAH-BIYDSLDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-oxooxan-3-yl]acetamide
• IUPAC Traditional name: N-[(3R,4R,5S,6R)-4,5-bis(benzyloxy)-6-[(benzyloxy)methyl]-2-oxooxan-3-yl]acetamide
• Synonyms: 2-(Acetylamino)-2-deoxy-3,4,6-tris-O-(phenylmethyl)-D-gluconic Acid δ-Lactone; 2-Acetamido-3,4,6-tri-O-benzyl-2-deoxy-D-glucono-1,5-lactone

Database IDs

• CAS Number: 34051-37-1
• PubChem SID: 162253077
• PubChem CID: 11812952

CALCULATED PROPERTIES

• Acid pKa: 12.017319
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 4.0694904
• LogD (pH = 7.4): 4.0694814
• Log P: 4.0694904
• Molar Refractivity: 133.9715 cm^3
• Polarizability: 53.08459 Å^3
• Polar Surface Area: 83.09 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; DMSO
• Apperance: Off-White Solid

REFERENCES

• Vocadlo, D., et al.: Biochem., 44, 12809 (2005)