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

• ChemBase ID: 161774
• Molecular Formular: C25H27NO8
• Molecular Mass: 469.48378
• Monoisotopic Mass: 469.17366683
• SMILES: [C@H]12[C@@H]([C@@H](CN([C@@H]1COC(O2)c1ccccc1)C(=O)OCc1ccccc1)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@@H]1CN(C(=O)OCc2ccccc2)[C@H]2[C@H]([C@@H]1OC(=O)C)OC(OC2)c1ccccc1
• InChI: InChI=1S/C25H27NO8/c1-16(27)32-21-13-26(25(29)31-14-18-9-5-3-6-10-18)20-15-30-24(19-11-7-4-8-12-19)34-22(20)23(21)33-17(2)28/h3-12,20-24H,13-15H2,1-2H3/t20-,21+,22-,23-,24?/m1/s1
• InChIKey: GQWUJUIVSOFDOW-QXNXEDLHSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 153373-52-5
• PubChem SID: 162255909
• PubChem CID: 53852602

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 3.1152935
• LogD (pH = 7.4): 3.1152935
• Log P: 3.1152935
• Molar Refractivity: 117.5631 cm^3
• Polarizability: 47.28698 Å^3
• Polar Surface Area: 100.6 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: White Powder

DETAILS

Toronto Research Chemicals - B286260

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

REFERENCES

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