N-[(2S,3S,4S)-3,6-dihydroxy-2-methyloxan-4-yl]-2,2,2-trifluoroacetamide

• ChemBase ID: 179003
• Molecular Formular: C8H12F3NO4
• Molecular Mass: 243.1803896
• Monoisotopic Mass: 243.07184253
• SMILES: [C@@H]1([C@@H](O)[C@H](NC(=O)C(F)(F)F)CC(O1)O)C
• Canonical SMILES: OC1C[C@@H](NC(=O)C(F)(F)F)[C@@H]([C@@H](O1)C)O
• InChI: InChI=1S/C8H12F3NO4/c1-3-6(14)4(2-5(13)16-3)12-7(15)8(9,10)11/h3-6,13-14H,2H2,1H3,(H,12,15)/t3-,4-,5?,6+/m0/s1
• InChIKey: KDSJJWJDPYHURS-HPASCFBVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3S,4S)-3,6-dihydroxy-2-methyloxan-4-yl]-2,2,2-trifluoroacetamide
• IUPAC Traditional name: N-[(2S,3S,4S)-3,6-dihydroxy-2-methyloxan-4-yl]-2,2,2-trifluoroacetamide
• Synonyms: 2,3,6-Trideoxy-3-[(trifluoroacetyl)amino]-L-lyxo-hexose; N-(Trifluoroacetamido)daunosamine

Database IDs

• CAS Number: 52471-40-6
• PubChem SID: 164234913
• PubChem CID: 11042934

CALCULATED PROPERTIES

• Acid pKa: 5.4474716
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -0.41620645
• LogD (pH = 7.4): -1.0479342
• Log P: -0.14069775
• Molar Refractivity: 44.9805 cm^3
• Polarizability: 17.729977 Å^3
• Polar Surface Area: 78.79 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - T781450

Intermediate in the production of Daunorubicin.

REFERENCES

• Alexander, J., et al.: J. Med. Chem., 27, 1343 (1984)