(4aR,6S,7S,8R,8aS)-6-methoxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diol

• ChemBase ID: 173374
• Molecular Formular: C14H18O6
• Molecular Mass: 282.28912
• Monoisotopic Mass: 282.1103383
• SMILES: [C@H]12[C@@H]([C@@H]([C@H](O[C@@H]1COC(O2)c1ccccc1)OC)O)O
• Canonical SMILES: CO[C@H]1O[C@@H]2COC(O[C@H]2[C@@H]([C@@H]1O)O)c1ccccc1
• InChI: InChI=1S/C14H18O6/c1-17-14-11(16)10(15)12-9(19-14)7-18-13(20-12)8-5-3-2-4-6-8/h2-6,9-16H,7H2,1H3/t9-,10-,11+,12-,13?,14+/m1/s1
• InChIKey: VVSWDMJYIDBTMV-ZWVDJKGDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6S,7S,8R,8aS)-6-methoxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diol
• IUPAC Traditional name: (4aR,6S,7S,8R,8aS)-6-methoxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diol
• Synonyms: Methyl 4,6-O-(Phenylmethylene)-α-D-mannopyranoside; Methyl 4,6-O-Benzylidenemannopyranoside; NSC 170162; Methyl 4,6-O-Benzylidene-α-D-mannopyranoside

Database IDs

• CAS Number: 4148-58-7
• PubChem SID: 164229284
• PubChem CID: 11065894

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.87566644
• LogD (pH = 7.4): 0.8756608
• Log P: 0.87566656
• Molar Refractivity: 67.5582 cm^3
• Polarizability: 27.693336 Å^3
• Polar Surface Area: 77.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 12.276533

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 141-143°C

Safety Information

• Storage Condition: Refrigerator

Product Information

• Classification: Rare Derivatives of Natural Compounds

DETAILS

Toronto Research Chemicals - M291500

Methyl 4,6-O-Benzylidene-α-D-mannopyranoside and its derivative were tested for in vitro antibacterial activity.

REFERENCES

• Grover, R., et al.: Phytopathol, 52, 876 (1962)
• Andary, C., et al.: Phytochem, 21, 1123 (1962)
• Singh, H., et al.: J. Agric. Food Chem., 38, 1483 (1962)