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

• ChemBase ID: 173372
• Molecular Formular: C14H18O6
• Molecular Mass: 282.28912
• Monoisotopic Mass: 282.1103383
• SMILES: C1(O[C@@H]2[C@@H](CO1)O[C@@H]([C@H]([C@H]2O)O)OC)c1ccccc1
• 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-BTZLDLHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6S,7R,8R,8aS)-6-methoxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxine-7,8-diol
• IUPAC Traditional name: (4aR,6S,7R,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-glucopyranoside; NSC 1681; Methyl 4,6-O-Benzylidene-α-D-glucopyranoside

Database IDs

• CAS Number: 3162-96-7
• PubChem SID: 164229282
• PubChem CID: 11822086

CALCULATED PROPERTIES

• Acid pKa: 12.276533
• 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

PROPERTIES

Physical Property

• Solubility: Chloroform; DMF; DMSO; Ethyl Acetate; Methanol
• Apperance: White Crystalline Solid
• Melting Point: 168-172°C

DETAILS

Toronto Research Chemicals - M291395

Methyl 4,6-O-Benzylidene-α-D-glucopyranoside is a derivative of methyl α-D-glucopyranoside tested for in vitro antibacterial activity.

REFERENCES

• Andary, C, et al.: Phytochem., 21, 1123 (1982)