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

• ChemBase ID: 177084
• Molecular Formular: C22H25NO10
• Molecular Mass: 463.4346
• Monoisotopic Mass: 463.14784601
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)OC(c1ccccc1)C#N)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: N#CC(c1ccccc1)O[C@@H]1O[C@@H](COC(=O)C)[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C22H25NO10/c1-12(24)28-11-18-19(29-13(2)25)20(30-14(3)26)21(31-15(4)27)22(33-18)32-17(10-23)16-8-6-5-7-9-16/h5-9,17-22H,11H2,1-4H3/t17?,18-,19-,20+,21-,22-/m1/s1
• InChIKey: QTSUMWNLKZZILY-XKYVVYCSSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 60981-47-7
• PubChem SID: 164232994
• PubChem CID: 71751863

CALCULATED PROPERTIES

• Acid pKa: 15.004974
• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 0.9474505
• LogD (pH = 7.4): 0.9474505
• Log P: 0.9474505
• Molar Refractivity: 106.7024 cm^3
• Polarizability: 43.592495 Å^3
• Polar Surface Area: 147.45 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - P839025

Protected (R)-Prunasin.

REFERENCES

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