(2R,3R,4S,5R)-4,5-bis(acetyloxy)-2-[(trichloroethanimidoyl)oxy]oxan-3-yl acetate

• ChemBase ID: 178868
• Molecular Formular: C13H16Cl3NO8
• Molecular Mass: 420.62704
• Monoisotopic Mass: 418.99414952
• SMILES: O1[C@@H]([C@H]([C@H]([C@@H](C1)OC(=O)C)OC(=O)C)OC(=O)C)OC(=N)C(Cl)(Cl)Cl
• Canonical SMILES: CC(=O)O[C@@H]1[C@H](OC[C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=N)C(Cl)(Cl)Cl
• InChI: InChI=1S/C13H16Cl3NO8/c1-5(18)22-8-4-21-11(25-12(17)13(14,15)16)10(24-7(3)20)9(8)23-6(2)19/h8-11,17H,4H2,1-3H3/t8-,9+,10-,11-/m1/s1
• InChIKey: NAGHJYXWJQCCPK-LMLFDSFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-4,5-bis(acetyloxy)-2-[(trichloroethanimidoyl)oxy]oxan-3-yl acetate
• IUPAC Traditional name: (2R,3R,4S,5R)-4,5-bis(acetyloxy)-2-[(trichloroethanimidoyl)oxy]oxan-3-yl acetate
• Synonyms: 2,3,4-Triacetate α-D-Xylopyranose 1-(2,2,2-Trichloroethanimidate); 2,3,4-Tri-O-acetyl-α-D-xylopyranosyl Trichloroacetimidate

Database IDs

• CAS Number: 128376-91-0
• PubChem SID: 164234778
• PubChem CID: 11122660

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.1908929
• LogD (pH = 7.4): 1.1942378
• Log P: 1.1942806
• Molar Refractivity: 94.8224 cm^3
• Polarizability: 34.49312 Å^3
• Polar Surface Area: 121.21 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 100-102°°

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - T767030

A xylose derivative for the treatment of proliferative disorders.

REFERENCES

• Roeser, K., et al.: Biochim. Biophys. Acta, 657, 321 (1981)
• Mega, T., et al.: J. Biochem., 94, 1637 (1981)
• Notenboom, V., et al.: Biochemistry, 37, 4751 (1981)