2-[(4aR,6R,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl]-2,3-dihydro-1H-isoindole-1,3-dione

• ChemBase ID: 173371
• Molecular Formular: C22H21NO7
• Molecular Mass: 411.40464
• Monoisotopic Mass: 411.13180202
• SMILES: [C@H]12[C@@H]([C@@H]([C@@H](O[C@@H]1COC(O2)c1ccccc1)OC)N1C(=O)c2c(C1=O)cccc2)O
• Canonical SMILES: CO[C@@H]1O[C@@H]2COC(O[C@H]2[C@@H]([C@@H]1N1C(=O)c2c(C1=O)cccc2)O)c1ccccc1
• InChI: InChI=1S/C22H21NO7/c1-27-22-16(23-19(25)13-9-5-6-10-14(13)20(23)26)17(24)18-15(29-22)11-28-21(30-18)12-7-3-2-4-8-12/h2-10,15-18,21-22,24H,11H2,1H3/t15-,16-,17-,18-,21?,22-/m1/s1
• InChIKey: LDLANDFJIIDMRD-CKKKZXOWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4aR,6R,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl]-2,3-dihydro-1H-isoindole-1,3-dione
• IUPAC Traditional name: 2-[(4aR,6R,7R,8R,8aS)-8-hydroxy-6-methoxy-2-phenyl-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-7-yl]isoindole-1,3-dione
• Synonyms: Methyl 2-Deoxy-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-4,6-O-(phenylmethylene)-β-D-glucopyranoside; Methyl 4,6-O-Benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside

Database IDs

• CAS Number: 97276-95-4
• PubChem SID: 164229281
• PubChem CID: 14655305

CALCULATED PROPERTIES

• Acid pKa: 13.310468
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 2.3113427
• LogD (pH = 7.4): 2.3113422
• Log P: 2.3113427
• Molar Refractivity: 103.5084 cm^3
• Polarizability: 40.475864 Å^3
• Polar Surface Area: 94.53 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - M291000

Methyl 4,6-O-Benzylidene-2-deoxy-2-N-phthalimido-β-D-glucopyranoside is used in the synthesis of the O-specific polysaccharide of Shigelia flexneri.

REFERENCES

• Kochetkov, N.K., et al.: Tetrahedron, 41, 3363 (1985)
• Koenig, A., et al.: Glycobiology, 7, 79 (1985)