methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(trichloroethanimidoyl)oxy]oxane-2-carboxylate

• ChemBase ID: 178859
• Molecular Formular: C15H18Cl3NO10
• Molecular Mass: 478.66312
• Monoisotopic Mass: 476.99962882
• SMILES: O(C(=N)C(Cl)(Cl)Cl)[C@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC
• Canonical SMILES: COC(=O)[C@@H]1O[C@H](OC(=N)C(Cl)(Cl)Cl)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C15H18Cl3NO10/c1-5(20)25-8-9(26-6(2)21)11(27-7(3)22)13(28-10(8)12(23)24-4)29-14(19)15(16,17)18/h8-11,13,19H,1-4H3/t8-,9-,10-,11+,13+/m0/s1
• InChIKey: KWNIVSQDHXVNAL-HKLXJQGRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(trichloroethanimidoyl)oxy]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(trichloroethanimidoyl)oxy]oxane-2-carboxylate
• Synonyms: Methyl-(2,3,4-tri-O-acetyl-α-D-glucopyranosyl Trichloroacetimidate)uronate; 2,3,4-Tri-O-acetyl-α-D-glucuronic Acid Methyl Ester, Trichloroacetimidate

Database IDs

• CAS Number: 92420-89-8
• PubChem SID: 164234769
• PubChem CID: 10961815

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.0264012
• LogD (pH = 7.4): 1.0300673
• Log P: 1.0301143
• Molar Refractivity: 105.4214 cm^3
• Polarizability: 39.063248 Å^3
• Polar Surface Area: 147.51 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-White to Pale Yellow Solid
• Melting Point: 103-105°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: Acid Sensitive, Temperature Sensitive

DETAILS

Toronto Research Chemicals - T765200

Intermediate for the synthesis of various glucuronide derivatives

REFERENCES

• Keinan et al.: J. Org. Chem. 49, 4988 (1984)
• Werschkun, B., et al.: J. Carbohyd. Chem., 18, 629 (1984)
• Tietze, L.F., et al.: J. Med. Chem., 52, 537 (1984)