(4aR,6S,7S,8R,8aR)-6,8-dimethoxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-ol

• ChemBase ID: 173375
• Molecular Formular: C15H20O6
• Molecular Mass: 296.3157
• Monoisotopic Mass: 296.12598836
• SMILES: [C@H]12[C@@H]([C@@H]([C@H](O[C@@H]1COC(O2)c1ccccc1)OC)O)OC
• Canonical SMILES: CO[C@H]1[C@@H]2OC(OC[C@H]2O[C@@H]([C@H]1O)OC)c1ccccc1
• InChI: InChI=1S/C15H20O6/c1-17-13-11(16)15(18-2)20-10-8-19-14(21-12(10)13)9-6-4-3-5-7-9/h3-7,10-16H,8H2,1-2H3/t10-,11+,12-,13-,14?,15+/m1/s1
• InChIKey: KCXVHILKGUDBTH-UISBESDSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6S,7S,8R,8aR)-6,8-dimethoxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-ol
• IUPAC Traditional name: (4aR,6S,7S,8R,8aR)-6,8-dimethoxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-ol
• Synonyms: Methyl 3-O-Methyl-4,6-O-(phenylmethylene)-α-D-mannopyranoside; Methyl 4,6-O-Benzylidene-3-O-methyl-α-D-mannopyranoside

Database IDs

• CAS Number: 52260-48-7
• PubChem SID: 164229285
• PubChem CID: 13730995

CALCULATED PROPERTIES

• Acid pKa: 12.365306
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.518793
• LogD (pH = 7.4): 1.5187883
• Log P: 1.518793
• Molar Refractivity: 72.3094 cm^3
• Polarizability: 29.589962 Å^3
• Polar Surface Area: 66.38 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M292100

Methyl 4,6-O-Benzylidene-3-O-methyl-α-D-mannopyranoside is used in the synthesis of mannooligosaccharides related to Mycobacterium smegmatis via dehydrative glycosylation.

REFERENCES

• ,Liao, W., et al.: Carbohydr. Res., 300, 347 (1997)
• Seitz, O., et al.: ChemBioChem., 1, 214 (1997)