(8R,8aS)-8-hydroxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl 4-methylbenzoate

• ChemBase ID: 160647
• Molecular Formular: C21H22O6
• Molecular Mass: 370.39578
• Monoisotopic Mass: 370.14163842
• SMILES: [C@H]12[C@@H](C(COC1COC(O2)c1ccccc1)OC(=O)c1ccc(cc1)C)O
• Canonical SMILES: O[C@@H]1C(COC2[C@H]1OC(OC2)c1ccccc1)OC(=O)c1ccc(cc1)C
• InChI: InChI=1S/C21H22O6/c1-13-7-9-14(10-8-13)20(23)26-16-11-24-17-12-25-21(27-19(17)18(16)22)15-5-3-2-4-6-15/h2-10,16-19,21-22H,11-12H2,1H3/t16?,17?,18-,19-,21?/m1/s1
• InChIKey: PGFGXGYVNALIEZ-JGQKGBITSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8R,8aS)-8-hydroxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl 4-methylbenzoate
• IUPAC Traditional name: (8R,8aS)-8-hydroxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl 4-methylbenzoate
• Synonyms: 1,5-Anhydro-4,6-O-(phenylmethylene)-D-glucitol 2-(4-Methylbenzoate); 1,5-Anhydro-4,6-O-benzylidene-2-O-p-toluoyl-D-glucitol

Database IDs

• CAS Number: 156715-23-0
• PubChem SID: 162254782
• PubChem CID: 46780401

CALCULATED PROPERTIES

• Acid pKa: 13.026954
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.6054852
• LogD (pH = 7.4): 3.6054842
• Log P: 3.6054852
• Molar Refractivity: 96.6403 cm^3
• Polarizability: 38.41236 Å^3
• Polar Surface Area: 74.22 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform
• Apperance: White Solid
• Melting Point: 140-142°C

DETAILS

Toronto Research Chemicals - A637700

An useful synthetic intermediate in the preparation of sugar nucleotides.

REFERENCES

• Verheggen, I, et al.: J. Med. Chem., 36, 2033-2040 (1993)