(3R,4S,5R)-3,5-bis(acetyloxy)-2-hydroxyoxan-4-yl acetate

• ChemBase ID: 178867
• Molecular Formular: C11H16O8
• Molecular Mass: 276.23994
• Monoisotopic Mass: 276.08451747
• SMILES: [C@@H]1([C@@H]([C@@H](C(OC1)O)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)O
• InChI: InChI=1S/C11H16O8/c1-5(12)17-8-4-16-11(15)10(19-7(3)14)9(8)18-6(2)13/h8-11,15H,4H2,1-3H3/t8-,9+,10-,11?/m1/s1
• InChIKey: NHLHTUYICZOCMA-GZBOUJLJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5R)-3,5-bis(acetyloxy)-2-hydroxyoxan-4-yl acetate
• IUPAC Traditional name: (3R,4S,5R)-3,5-bis(acetyloxy)-2-hydroxyoxan-4-yl acetate
• Synonyms: D-Xylose 2,3,4-Triacetate; 2,3,4-Tri-O-acetyl-D-xylose; 2,3,4-Tri-O-acetyl-D-xylopyranose

Database IDs

• CAS Number: 55018-54-7
• PubChem SID: 164234777
• PubChem CID: 14077888

CALCULATED PROPERTIES

• Acid pKa: 11.327877
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.97882867
• LogD (pH = 7.4): -0.9788793
• Log P: -0.9788281
• Molar Refractivity: 57.4154 cm^3
• Polarizability: 24.196152 Å^3
• Polar Surface Area: 108.36 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

DETAILS

Toronto Research Chemicals - T767020

2,3,4-Tri-O-acetyl-D-xylopyranose is used in the synthesis of D-xylopyranose series: tri-O-acetyl-D-xyloses and chloroacetyl derivatives.

REFERENCES

• Utille, J.P., et al.: Carbohydr. Res., 106(1)
• 43 (1)