(3S,4R)-3-(acetyloxy)-5-acetamido-6-hydroxy-2-(hydroxymethyl)oxan-4-yl acetate

• ChemBase ID: 159287
• Molecular Formular: C12H19NO8
• Molecular Mass: 305.28116
• Monoisotopic Mass: 305.11106657
• SMILES: [C@@H]1([C@@H](C(C(OC1CO)O)NC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: OCC1OC(O)C([C@H]([C@@H]1OC(=O)C)OC(=O)C)NC(=O)C
• InChI: InChI=1S/C12H19NO8/c1-5(15)13-9-11(20-7(3)17)10(19-6(2)16)8(4-14)21-12(9)18/h8-12,14,18H,4H2,1-3H3,(H,13,15)/t8?,9?,10-,11-,12?/m1/s1
• InChIKey: JCTNUTZHSLBEBB-AWKVMXQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4R)-3-(acetyloxy)-5-acetamido-6-hydroxy-2-(hydroxymethyl)oxan-4-yl acetate
• IUPAC Traditional name: (3S,4R)-3-(acetyloxy)-5-acetamido-6-hydroxy-2-(hydroxymethyl)oxan-4-yl acetate
• Synonyms: 2-(Acetylamino)-2-deoxy-D-glucopyranose 3,4-Diacetate; (N,3-O,4-O)-Triacetyl-D-Glucosamine; N-Acetyl-D-Glucosamine 3,4-Diacetate

Database IDs

• PubChem SID: 162253422
• PubChem CID: 71312900

CALCULATED PROPERTIES

• Acid pKa: 11.6033945
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -2.338324
• LogD (pH = 7.4): -2.33835
• Log P: -2.3383236
• Molar Refractivity: 65.3277 cm^3
• Polarizability: 27.107702 Å^3
• Polar Surface Area: 131.39 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 172-176°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A178215

A triacetylated analogue of D-Glucosamine (G514950).