(4S,5S,6S)-6-methyl-5-(4-nitrobenzoyloxy)-4-(trifluoroacetamido)oxan-2-yl 4-nitrobenzoate

• ChemBase ID: 179004
• Molecular Formular: C22H18F3N3O10
• Molecular Mass: 541.3876296
• Monoisotopic Mass: 541.09442845
• SMILES: [C@@H]1([C@H]([C@@H](CC(O1)OC(=O)c1ccc(cc1)[N+](=O)[O-])NC(=O)C(F)(F)F)OC(=O)c1ccc(cc1)[N+](=O)[O-])C
• Canonical SMILES: C[C@@H]1OC(C[C@H]([C@@H]1OC(=O)c1ccc(cc1)[N+](=O)[O-])NC(=O)C(F)(F)F)OC(=O)c1ccc(cc1)[N+](=O)[O-]
• InChI: InChI=1S/C22H18F3N3O10/c1-11-18(38-20(30)13-4-8-15(9-5-13)28(34)35)16(26-21(31)22(23,24)25)10-17(36-11)37-19(29)12-2-6-14(7-3-12)27(32)33/h2-9,11,16-18H,10H2,1H3,(H,26,31)/t11-,16-,17?,18+/m0/s1
• InChIKey: BEUSXTJFSNEHDV-SWAJYTQSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S,5S,6S)-6-methyl-5-(4-nitrobenzoyloxy)-4-(trifluoroacetamido)oxan-2-yl 4-nitrobenzoate
• IUPAC Traditional name: (4S,5S,6S)-6-methyl-5-(4-nitrobenzoyloxy)-4-(trifluoroacetamido)oxan-2-yl 4-nitrobenzoate
• Synonyms: 2,3,6-Trideoxy-3-[(trifluoroacetyl)amino]-lyxo-hexopyranose 1,4-Bis(4-nitrobenzoate); N-Trifluoroacetamido-1,4-di-p-nitrobenzoyl Daunosamine

Database IDs

• CAS Number: 52583-22-9
• PubChem SID: 164234914
• PubChem CID: 10768819

CALCULATED PROPERTIES

• Acid pKa: 5.0603237
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): 4.274135
• LogD (pH = 7.4): 3.8020236
• Log P: 4.7298703
• Molar Refractivity: 119.2739 cm^3
• Polarizability: 44.569912 Å^3
• Polar Surface Area: 182.57 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - T781500

Intermediate in the production of Daunorubicin.