(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-{[(4-nitrophenyl)methyl]sulfanyl}oxane-3,4,5-triol

• ChemBase ID: 175226
• Molecular Formular: C13H17NO7S
• Molecular Mass: 331.34158
• Monoisotopic Mass: 331.07257289
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)SCc1ccc(cc1)[N+](=O)[O-])O)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](SCc2ccc(cc2)[N+](=O)[O-])[C@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C13H17NO7S/c15-5-9-10(16)11(17)12(18)13(21-9)22-6-7-1-3-8(4-2-7)14(19)20/h1-4,9-13,15-18H,5-6H2/t9-,10+,11+,12-,13+/m1/s1
• InChIKey: PMQUMUZAQBRAKI-SJHCENCUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-{[(4-nitrophenyl)methyl]sulfanyl}oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-{[(4-nitrophenyl)methyl]sulfanyl}oxane-3,4,5-triol
• Synonyms: (4-Nitrophenyl)methyl 1-Thio-β-D-galactopyranoside; 4-Nitrobenzyl 1-Thio-β-D-galactopryranoside

Database IDs

• CAS Number: 35785-19-4
• PubChem SID: 164231136
• PubChem CID: 71751057

CALCULATED PROPERTIES

• Acid pKa: 12.480158
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -0.017742207
• LogD (pH = 7.4): -0.017745769
• Log P: -0.01774216
• Molar Refractivity: 78.7813 cm^3
• Polarizability: 30.78555 Å^3
• Polar Surface Area: 135.97 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; DMSO
• Apperance: Off-White Solid
• Melting Point: 184-186°C

Safety Information

• Storage Condition: -20°C Freezer
• Storage Warning: Moisture, Temperature Sensitive

DETAILS

Toronto Research Chemicals - N495750

Used in the synthesis of 1-thio-β-D-glycopyranosides.

REFERENCES

• Claeyssens, M., et al.: Carbohydrate Res., 22, 460 (1972)