(4aR,6R,7R,8R,8aR)-7-acetamido-2-phenyl-6-[(trichloroethanimidoyl)oxy]-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-8-yl acetate

• ChemBase ID: 158878
• Molecular Formular: C19H21Cl3N2O7
• Molecular Mass: 495.73824
• Monoisotopic Mass: 494.04143406
• SMILES: [C@@H]12[C@@H]([C@@H]([C@H](O[C@@H]1COC(O2)c1ccccc1)OC(=N)C(Cl)(Cl)Cl)NC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@H]1[C@H]2OC(OC[C@H]2O[C@@H]([C@H]1NC(=O)C)OC(=N)C(Cl)(Cl)Cl)c1ccccc1
• InChI: InChI=1S/C19H21Cl3N2O7/c1-9(25)24-13-15(28-10(2)26)14-12(29-17(13)31-18(23)19(20,21)22)8-27-16(30-14)11-6-4-3-5-7-11/h3-7,12-17,23H,8H2,1-2H3,(H,24,25)/t12-,13-,14+,15-,16?,17-/m1/s1
• InChIKey: BITIXZADLMPSAR-ZKSLVMDMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6R,7R,8R,8aR)-7-acetamido-2-phenyl-6-[(trichloroethanimidoyl)oxy]-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-8-yl acetate
• IUPAC Traditional name: (4aR,6R,7R,8R,8aR)-7-acetamido-2-phenyl-6-[(trichloroethanimidoyl)oxy]-hexahydro-2H-pyrano[3,2-d][1,3]dioxin-8-yl acetate
• Synonyms: 2-(Acetylamino)-2-deoxy-4,6-O-(phenylmethylene)-α-D-galactopyranose 3-Acetate 1-(2,2,2-Trichloroethanimidate); 2-(Acetylamino)-2-deoxy-3-O-acetyl-4,6-O-benzylidene-α-D-galactopyranose Trichloroacetimidate

Database IDs

• CAS Number: 171973-69-6
• PubChem SID: 162253013
• PubChem CID: 71312726

CALCULATED PROPERTIES

• Acid pKa: 10.818111
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 2.5548005
• LogD (pH = 7.4): 2.5585423
• Log P: 2.558739
• Molar Refractivity: 120.4668 cm^3
• Polarizability: 44.155937 Å^3
• Polar Surface Area: 116.17 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - A150850

Intermediate in the preparation of the T epitope of Threonyl