(2S,3S,4R,5S,6S)-2-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol

• ChemBase ID: 175171
• Molecular Formular: C18H25NO12
• Molecular Mass: 447.3906
• Monoisotopic Mass: 447.13767525
• SMILES: [C@H]1([C@@H]([C@@H]([C@H](O[C@H]1CO)Oc1ccc(cc1)[N+](=O)[O-])O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C)O)O)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@H](Oc2ccc(cc2)[N+](=O)[O-])[C@H]([C@H]([C@H]1O)O)O[C@@H]1O[C@@H](C)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C18H25NO12/c1-7-11(21)13(23)15(25)17(28-7)31-16-14(24)12(22)10(6-20)30-18(16)29-9-4-2-8(3-5-9)19(26)27/h2-5,7,10-18,20-25H,6H2,1H3/t7-,10+,11+,12-,13+,14-,15-,16+,17-,18-/m0/s1
• InChIKey: FMNXEBSKDAQHBI-FNTPIXKUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5S,6S)-2-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol
• IUPAC Traditional name: (2S,3S,4R,5S,6S)-2-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-(4-nitrophenoxy)oxan-3-yl]oxy}-6-methyloxane-3,4,5-triol
• Synonyms: 4-Nitrophenyl 2-O-(6-Deoxy-α-L-galactopyranosyl)-α-D-galactopyranoside; 4-Nitrophenyl 2-O-(α-L-Fucopyranosyl)-α-D-galactopyranoside

Database IDs

• CAS Number: 383417-46-7
• PubChem SID: 164231081
• PubChem CID: 71307219

CALCULATED PROPERTIES

• Acid pKa: 12.10016
• H Acceptors: 12
• H Donor: 6
• LogD (pH = 5.5): -1.3823292
• LogD (pH = 7.4): -1.3823377
• Log P: -1.3823291
• Molar Refractivity: 98.3776 cm^3
• Polarizability: 39.75317 Å^3
• Polar Surface Area: 204.12 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Warm Methanol
• Apperance: White Amorphous Solid
• Melting Point: 257-259°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - N503550

Nitrophenyl derivative of 2-O-(a-L-Fucopyranosyl)-a-D-galactopyranoside (Disaccharide H), a biologically important oligosaccharide component of glycoconjugates that play a role in cellular recognition and intercellular interactions.

REFERENCES

• Carbohyd. Res., 4, 189 (1967)
• Can. J. Chem., 59, 314 (1967)
• J. Carbohydrate Chem., 11(1967)
• 397 (1992)