[(2S,3S,4S,5S)-3,4-bis(acetyloxy)-5-{4,6-dichloro-1H-imidazo[4,5-c]pyridin-1-yl}oxolan-2-yl]methyl acetate

• ChemBase ID: 178864
• Molecular Formular: C17H17Cl2N3O7
• Molecular Mass: 446.23878
• Monoisotopic Mass: 445.04435526
• SMILES: n1c(cc2c(c1Cl)ncn2[C@@H]1[C@H]([C@H]([C@@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)Cl
• Canonical SMILES: CC(=O)O[C@H]1[C@@H](OC(=O)C)[C@@H](O[C@@H]1n1cnc2c1cc(Cl)nc2Cl)COC(=O)C
• InChI: InChI=1S/C17H17Cl2N3O7/c1-7(23)26-5-11-14(27-8(2)24)15(28-9(3)25)17(29-11)22-6-20-13-10(22)4-12(18)21-16(13)19/h4,6,11,14-15,17H,5H2,1-3H3/t11-,14-,15-,17-/m0/s1
• InChIKey: QUGRSJQZWTYDHN-SIUGBPQLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2S,3S,4S,5S)-3,4-bis(acetyloxy)-5-{4,6-dichloro-1H-imidazo[4,5-c]pyridin-1-yl}oxolan-2-yl]methyl acetate
• IUPAC Traditional name: [(2S,3S,4S,5S)-3,4-bis(acetyloxy)-5-{4,6-dichloroimidazo[4,5-c]pyridin-1-yl}oxolan-2-yl]methyl acetate
• Synonyms: 4,6-Dichloro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-imidazo[4,5-c]pyridine; 1-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-4,6-dichloroimidazo[4,5-c]pyridine

Database IDs

• CAS Number: 63423-94-9
• PubChem SID: 164234774
• PubChem CID: 71752665

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 1.4532028
• LogD (pH = 7.4): 1.4536941
• Log P: 1.4537004
• Molar Refractivity: 98.5946 cm^3
• Polarizability: 40.444412 Å^3
• Polar Surface Area: 118.84 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off-White Solid
• Melting Point: 239-242°C

DETAILS

Toronto Research Chemicals - T767013

1-(2,3,5-Tri-O-acetyl-β-D-ribofuranosyl)-4,6-dichloroimidazo[4,5-c]pyridine is an intermediate of 3-Deazaadenosine (D200875).

REFERENCES

• Hotzel, I., et al.: Virus Res., 69, 47 (2000)
• Vittori, S., et al.: J. Med. Chem., 43, 250 (2000)
• Salvatori, D., et al.: Comp. Immunol. Microb., 24, 113 (2000)