(3R,4S,5R)-2,3,5-tris(acetyloxy)oxan-4-yl acetate

• ChemBase ID: 178233
• Molecular Formular: C13H18O9
• Molecular Mass: 318.27662
• Monoisotopic Mass: 318.09508216
• SMILES: [C@@H]1([C@@H]([C@@H](C(OC1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@@H]1COC([C@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C13H18O9/c1-6(14)19-10-5-18-13(22-9(4)17)12(21-8(3)16)11(10)20-7(2)15/h10-13H,5H2,1-4H3/t10-,11+,12-,13?/m1/s1
• InChIKey: MJOQJPYNENPSSS-DAAZQVBGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5R)-2,3,5-tris(acetyloxy)oxan-4-yl acetate
• IUPAC Traditional name: (3R,4S,5R)-2,3,5-tris(acetyloxy)oxan-4-yl acetate
• Synonyms: Xylopyranose Tetraacetate; DL-Xylopyranose Tetraacetate; 1,2,3,4-Tetra-O-acetyl-D-xylopyranose

Database IDs

• CAS Number: 62929-49-1
• PubChem SID: 164234143
• PubChem CID: 11267112

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): -0.5377026
• LogD (pH = 7.4): -0.5377026
• Log P: -0.5377026
• Molar Refractivity: 66.5669 cm^3
• Polarizability: 28.05088 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate,
• Apperance: White Solid
• Melting Point: 42-44°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T283910

1,2,3,4-Tetra-O-acetyl-D-xylopyranose is used in the synthesis of monosaccharides by oxidation of furfural derivatives.

REFERENCES

• Bognar, R., et al.: Carbohydr. Res., 52, 11 (1976)