N-[(3R,4R,5S,6R)-5-{[(2S,3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy}-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide

• ChemBase ID: 158883
• Molecular Formular: C14H25NO11
• Molecular Mass: 383.3484
• Monoisotopic Mass: 383.14276063
• SMILES: [C@H]1([C@@H]([C@@H](O[C@H]1O[C@H]1[C@@H]([C@@H](C(O[C@H]1CO)O)NC(=O)C)O)[C@H](O)CO)O)O
• Canonical SMILES: OC[C@@H]1OC(O)[C@H]([C@H]([C@@H]1O[C@@H]1O[C@H]([C@H]([C@H]1O)O)[C@@H](CO)O)O)NC(=O)C
• InChI: InChI=1S/C14H25NO11/c1-4(18)15-7-8(20)12(6(3-17)24-13(7)23)26-14-10(22)9(21)11(25-14)5(19)2-16/h5-14,16-17,19-23H,2-3H2,1H3,(H,15,18)/t5?,6-,7-,8-,9-,10-,11+,12-,13?,14+/m1/s1
• InChIKey: XDJSTHFKZUCWKK-VHSAZRKYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(3R,4R,5S,6R)-5-{[(2S,3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy}-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(3R,4R,5S,6R)-5-{[(2S,3R,4R,5S)-5-[(1R)-1,2-dihydroxyethyl]-3,4-dihydroxyoxolan-2-yl]oxy}-2,4-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• Synonyms: Galf1-β-4-GlcNAc; 2-Acetamido-2-deoxy-4-O-(β-D-galactofuranosyl)-α,β-D-glucopyranose

Database IDs

• PubChem SID: 162253018
• PubChem CID: 71298077

CALCULATED PROPERTIES

• Acid pKa: 11.49752
• H Acceptors: 11
• H Donor: 8
• LogD (pH = 5.5): -4.9914103
• LogD (pH = 7.4): -4.9914436
• Log P: -4.9914103
• Molar Refractivity: 79.438 cm^3
• Polarizability: 33.212086 Å^3
• Polar Surface Area: 198.4 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 127-129°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A151750

Synthetic galactofuranose-containing oligosaccharides could be useful for the identification of strains of T. cruzi as well as for studies on the inhibition of the biosynthesis of these unique O-linked chains.

REFERENCES

• Gallo-Rodriguez, C., et al.: J. Org. Chem., 61, 1886 (1996)