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

• ChemBase ID: 160394
• Molecular Formular: C14H20N2O6
• Molecular Mass: 312.3184
• Monoisotopic Mass: 312.13213637
• SMILES: [C@H]1([C@@H]([C@@H]([C@H](O[C@H]1CO)Oc1ccc(cc1)N)NC(=O)C)O)O
• Canonical SMILES: OC[C@@H]1O[C@H](Oc2ccc(cc2)N)[C@H]([C@H]([C@H]1O)O)NC(=O)C
• InChI: InChI=1S/C14H20N2O6/c1-7(18)16-11-13(20)12(19)10(6-17)22-14(11)21-9-4-2-8(15)3-5-9/h2-5,10-14,17,19-20H,6,15H2,1H3,(H,16,18)/t10-,11-,12+,13-,14+/m1/s1
• InChIKey: RWZITXGZJXXMRL-RGDJUOJXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2R,3R,4R,5R,6R)-2-(4-aminophenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2R,3R,4R,5R,6R)-2-(4-aminophenoxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: 4-Aminophenyl 2-(Acetylamino)-2-deoxy-α-D-galactopyranoside Monohydrochloride; 4-Aminophenyl 2-Acetamido-2-deoxy-α-D-galactopyranoside Hydrochloride

Database IDs

• CAS Number: 210049-16-4
• PubChem SID: 162254529
• PubChem CID: 29971815

CALCULATED PROPERTIES

• Acid pKa: 12.266892
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): -1.7827965
• LogD (pH = 7.4): -1.7162726
• Log P: -1.7153487
• Molar Refractivity: 75.985 cm^3
• Polarizability: 30.045935 Å^3
• Polar Surface Area: 134.27 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: White Solid
• Melting Point: 183-185°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A622000

A galactoside aminodeoxy nitrophenyl used in synthetic preparation.

REFERENCES

• Petitou, M., et al.: Carbohydrate Res., 42, 180 (1975)