(8R,8aS)-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diol

• ChemBase ID: 160646
• Molecular Formular: C13H16O5
• Molecular Mass: 252.26314
• Monoisotopic Mass: 252.09977361
• SMILES: [C@H]12[C@@H](C(COC1COC(O2)c1ccccc1)O)O
• Canonical SMILES: OC1COC2[C@H]([C@@H]1O)OC(OC2)c1ccccc1
• InChI: InChI=1S/C13H16O5/c14-9-6-16-10-7-17-13(18-12(10)11(9)15)8-4-2-1-3-5-8/h1-5,9-15H,6-7H2/t9?,10?,11-,12-,13?/m1/s1
• InChIKey: KRNWQNYQBBRLMC-JBSNKVJHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8R,8aS)-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diol
• IUPAC Traditional name: (8R,8aS)-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diol
• Synonyms: 1,5-Anhydro-4,6-O-(phenylmethylene)-D-glucitol; 1,5-Anhydro-4,6-O-benzylidene- sorbitol; 1,5-Anhydro-4,6-O-benzylidene-D-glucitol

Database IDs

• CAS Number: 65190-39-8
• PubChem SID: 162254781
• PubChem CID: 46780400

CALCULATED PROPERTIES

• Acid pKa: 12.879422
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 0.59676397
• LogD (pH = 7.4): 0.59676254
• Log P: 0.59676397
• Molar Refractivity: 61.7771 cm^3
• Polarizability: 25.12832 Å^3
• Polar Surface Area: 68.15 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform
• Apperance: White Solid
• Melting Point: 160-163°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - A637690

An useful synthetic intermediate in the preparation of sugar nucleotides.

REFERENCES

• Verheggen, I., et al.: J. Med. Chem., 36, 2033 (1993)