[(2R,3S,4R,5R,6R)-3,4-bis(acetyloxy)-5-acetamido-6-methoxyoxan-2-yl]methyl acetate

• ChemBase ID: 173212
• Molecular Formular: C15H23NO9
• Molecular Mass: 361.34442
• Monoisotopic Mass: 361.13728132
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)OC)NC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CO[C@@H]1O[C@@H](COC(=O)C)[C@H]([C@@H]([C@@H]1NC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C15H23NO9/c1-7(17)16-12-14(24-10(4)20)13(23-9(3)19)11(6-22-8(2)18)25-15(12)21-5/h11-15H,6H2,1-5H3,(H,16,17)/t11-,12-,13-,14-,15-/m1/s1
• InChIKey: BKJUFVXNIJMMKO-KJWHEZOQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R,6R)-3,4-bis(acetyloxy)-5-acetamido-6-methoxyoxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4R,5R,6R)-3,4-bis(acetyloxy)-5-acetamido-6-methoxyoxan-2-yl]methyl acetate
• Synonyms: GlcNAc1-β-OMe; Methyl N-Acetyl-β-D-glucosaminide; β-Methyl N-Acetylglucosaminide; Methyl 2-Acetamido-2-deoxy-β-D-glucopyranoside; GlcNAc1-β-OMe Triacetate; Methyl N-Acetyl-β-D-glucosaminide Triacetate; β-Methyl N-Acetylglucosaminide Triacetate; Methyl 2-Acetamido-2-deoxy-β-D-glucopyranoside Triacetate

Database IDs

• CAS Number: 3946-01-8; 2771-48-4
• PubChem SID: 164229122
• PubChem CID: 10784799

CALCULATED PROPERTIES

• Acid pKa: 12.237012
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -1.254072
• LogD (pH = 7.4): -1.2540773
• Log P: -1.2540717
• Molar Refractivity: 79.2304 cm^3
• Polarizability: 32.838516 Å^3
• Polar Surface Area: 126.46 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: >192°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M275235

Protected Glucosamine derivative.

REFERENCES

• Tsuda, Y., et al.: Chem., Pharm. Bull., 37, 2673 (1989)