(2R,3R,4R,5S)-4-[(2,4-dichlorophenyl)methoxy]-2-{[(2,4-dichlorophenyl)methoxy]methyl}-5-methoxyoxolan-3-ol

• ChemBase ID: 173393
• Molecular Formular: C20H20Cl4O5
• Molecular Mass: 482.1818
• Monoisotopic Mass: 480.00648446
• SMILES: [C@H]1([C@@H]([C@H](O[C@@H]1OC)COCc1ccc(cc1Cl)Cl)O)OCc1ccc(cc1Cl)Cl
• Canonical SMILES: CO[C@H]1O[C@@H]([C@H]([C@H]1OCc1ccc(cc1Cl)Cl)O)COCc1ccc(cc1Cl)Cl
• InChI: InChI=1S/C20H20Cl4O5/c1-26-20-19(28-9-12-3-5-14(22)7-16(12)24)18(25)17(29-20)10-27-8-11-2-4-13(21)6-15(11)23/h2-7,17-20,25H,8-10H2,1H3/t17-,18-,19-,20+/m1/s1
• InChIKey: DCSASUHYUNVYBF-WTGUMLROSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S)-4-[(2,4-dichlorophenyl)methoxy]-2-{[(2,4-dichlorophenyl)methoxy]methyl}-5-methoxyoxolan-3-ol
• IUPAC Traditional name: (2R,3R,4R,5S)-4-[(2,4-dichlorophenyl)methoxy]-2-{[(2,4-dichlorophenyl)methoxy]methyl}-5-methoxyoxolan-3-ol
• Synonyms: Methyl 3,5-Bis-O-[(2,4-dichlorophenyl)methyl]-α-D-ribofuranoside; 1-O-Methyl 3,5-Bis-O-(2,4-dichlorobenzyl)-α-D-ribofuranoside; Methyl 3,5-Bis-O-(2,4-dichlorobenzyl)-α-D-ribofuranoside

Database IDs

• CAS Number: 168427-35-8
• PubChem SID: 164229303
• PubChem CID: 71750231

CALCULATED PROPERTIES

• Acid pKa: 12.976063
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 5.4923
• LogD (pH = 7.4): 5.492299
• Log P: 5.4923
• Molar Refractivity: 112.6589 cm^3
• Polarizability: 44.975784 Å^3
• Polar Surface Area: 57.15 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M294150

An intermediate in the synthesis of nucleoside compounds and derivatives suitable for use in treating or prophylaxis of an infection by the SARS virus and/or in treating or prophylaxis of SARS, and for use in inhibiting replication of the SARS virus.

REFERENCES

• Eldrup, A.B., et al.: J. Med. Chem., 47, 5284 (2004)