benzyl (8R,8aR)-7,8-dihydroxy-2-phenyl-octahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylate

• ChemBase ID: 161773
• Molecular Formular: C21H23NO6
• Molecular Mass: 385.41042
• Monoisotopic Mass: 385.15253746
• SMILES: [C@H]12[C@@H](C(CN(C1COC(O2)c1ccccc1)C(=O)OCc1ccccc1)O)O
• Canonical SMILES: OC1CN(C(=O)OCc2ccccc2)C2[C@H]([C@@H]1O)OC(OC2)c1ccccc1
• InChI: InChI=1S/C21H23NO6/c23-17-11-22(21(25)27-12-14-7-3-1-4-8-14)16-13-26-20(28-19(16)18(17)24)15-9-5-2-6-10-15/h1-10,16-20,23-24H,11-13H2/t16?,17?,18-,19-,20?/m1/s1
• InChIKey: GBRJHLWAZWZRJM-KZBHQWPGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl (8R,8aR)-7,8-dihydroxy-2-phenyl-octahydro-[1,3]dioxino[5,4-b]pyridine-5-carboxylate
• IUPAC Traditional name: benzyl (8R,8aR)-7,8-dihydroxy-2-phenyl-hexahydro-2H-[1,3]dioxino[5,4-b]pyridine-5-carboxylate
• Synonyms: (2R,4aR,7S,8R,8aR)-Hexahydro-7,8-dihydroxy-2-phenyl-5H-1,3-dioxino[5,4-b]pyridine-5-carboxylic Acid Phenylmethyl Ester; N-Benzyloxycarbonyl-4,6-O-phenylmethylene Deoxynojirimycin

Database IDs

• CAS Number: 138381-83-6
• PubChem SID: 162255908
• PubChem CID: 71313887

CALCULATED PROPERTIES

• Acid pKa: 13.029886
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.2330425
• LogD (pH = 7.4): 2.2330415
• Log P: 2.2330425
• Molar Refractivity: 99.2601 cm^3
• Polarizability: 39.58955 Å^3
• Polar Surface Area: 88.46 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White Powder

DETAILS

Toronto Research Chemicals - B286255

Deoxynojirimycin (D245000) derivative. Reactant in the preparation of sialoglycoconjugates.

REFERENCES

• Kiso, M. et al.; J. Carbohyd. Chem. 12, 985 (1993)