[(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[(R)-carbamoyl(phenyl)methoxy]oxan-2-yl]methyl acetate

• ChemBase ID: 178212
• Molecular Formular: C22H27NO11
• Molecular Mass: 481.44988
• Monoisotopic Mass: 481.15841069
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)O[C@@H](C(=O)N)c1ccccc1)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)OC[C@@H]1O[C@@H](O[C@H](c2ccccc2)C(=O)N)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C22H27NO11/c1-11(24)29-10-16-18(30-12(2)25)19(31-13(3)26)20(32-14(4)27)22(33-16)34-17(21(23)28)15-8-6-5-7-9-15/h5-9,16-20,22H,10H2,1-4H3,(H2,23,28)/t16-,17-,18-,19+,20-,22+/m1/s1
• InChIKey: QXCHUKFHDDLXBX-MRVGAPFNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[(R)-carbamoyl(phenyl)methoxy]oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-[(R)-carbamoyl(phenyl)methoxy]oxan-2-yl]methyl acetate
• Synonyms: (αR)-α-[(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)oxy]benzeneacetamide

Database IDs

• CAS Number: 207512-68-3
• PubChem SID: 164234122
• PubChem CID: 71752391

CALCULATED PROPERTIES

• Acid pKa: 14.99413
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 0.08255903
• LogD (pH = 7.4): 0.082559034
• Log P: 0.08255903
• Molar Refractivity: 109.5453 cm^3
• Polarizability: 44.999577 Å^3
• Polar Surface Area: 166.75 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - T280795

(R)-Prunasin intermediate.

REFERENCES

• Nakajima, N., et al.: Biosci., Biotechnol., Biochem., 62, 453 (1998)