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

• ChemBase ID: 158908
• Molecular Formular: C8H16N2O5
• Molecular Mass: 220.22304
• Monoisotopic Mass: 220.10592162
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)N)NC(=O)C)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](N)[C@H]([C@H]([C@@H]1O)O)NC(=O)C
• InChI: InChI=1S/C8H16N2O5/c1-3(12)10-5-7(14)6(13)4(2-11)15-8(5)9/h4-8,11,13-14H,2,9H2,1H3,(H,10,12)/t4-,5-,6-,7-,8-/m1/s1
• InChIKey: MCGXOCXFFNKASF-FMDGEEDCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4R,5S,6R)-2-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-acetyl-β-D-glucosaminylamine
• Synonyms: 2-Acetamido-2-deoxy-β-D-glucosylamine

Database IDs

• CAS Number: 4229-38-3
• PubChem SID: 162253043
• PubChem CID: 439454

CALCULATED PROPERTIES

• Acid pKa: 12.507108
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -4.792502
• LogD (pH = 7.4): -3.4623196
• Log P: -3.3274562
• Molar Refractivity: 48.6822 cm^3
• Polarizability: 20.21645 Å^3
• Polar Surface Area: 125.04 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Light Brown Solid
• Melting Point: 103-112°C dec.

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A158250

Used mainly for the synthesis of various 1-N-acyl derivatives which model the N-glycosylamine linkage of glycoproteins.

REFERENCES

• Harmat, N., et al.: Bioorg. Med. Chem. Lett., 12, 693 (2002)
• Fedi, V., et al.: J. Med. Chem., 47, 6935 (2002)
• Kato, M., et al.: Bioorg. Med. Chem., 13, 1563 (2002)