(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-isothiocyanatophenoxy)oxane-3,4,5-triol

• ChemBase ID: 171987
• Molecular Formular: C13H15NO6S
• Molecular Mass: 313.3263
• Monoisotopic Mass: 313.06200821
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H](O[C@H]1CO)Oc1ccc(cc1)N=C=S)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@H](Oc2ccc(cc2)N=C=S)[C@H]([C@H]([C@@H]1O)O)O
• InChI: InChI=1S/C13H15NO6S/c15-5-9-10(16)11(17)12(18)13(20-9)19-8-3-1-7(2-4-8)14-6-21/h1-4,9-13,15-18H,5H2/t9-,10-,11+,12-,13+/m1/s1
• InChIKey: RWANFUZQWINQBY-LBELIVKGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-isothiocyanatophenoxy)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-(4-isothiocyanatophenoxy)oxane-3,4,5-triol
• Synonyms: α-D-Glucopyranosylphenyl p-Isothiocyanate; 4-Isothiocyanatophenyl α-D-Glucopyranoside

Database IDs

• CAS Number: 20581-45-7
• PubChem SID: 164227897
• PubChem CID: 29982549

CALCULATED PROPERTIES

• Acid pKa: 12.200142
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 0.42343524
• LogD (pH = 7.4): 0.4234307
• Log P: 0.42343763
• Molar Refractivity: 77.2462 cm^3
• Polarizability: 30.287663 Å^3
• Polar Surface Area: 111.74 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - I905100

A useful substrate for the preparation of neoglycoproteins.

REFERENCES

• Monsigny, M., et al.: Biol. Cell, 51, 187 (1984)