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

• ChemBase ID: 173392
• Molecular Formular: C20H18Cl4O5
• Molecular Mass: 480.16592
• Monoisotopic Mass: 477.9908344
• SMILES: [C@H]1(C(=O)[C@H](O[C@@H]1OC)COCc1ccc(cc1Cl)Cl)OCc1ccc(cc1Cl)Cl
• Canonical SMILES: CO[C@H]1O[C@@H](C(=O)[C@H]1OCc1ccc(cc1Cl)Cl)COCc1ccc(cc1Cl)Cl
• InChI: InChI=1S/C20H18Cl4O5/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/h2-7,17,19-20H,8-10H2,1H3/t17-,19-,20+/m1/s1
• InChIKey: ALWALZTVIADTRS-RLLQIKCJSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 443642-30-6
• PubChem SID: 164229302
• PubChem CID: 71750230

CALCULATED PROPERTIES

• Acid pKa: 16.60743
• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 6.107476
• LogD (pH = 7.4): 6.107476
• Log P: 6.107476
• Molar Refractivity: 111.8922 cm^3
• Polarizability: 44.43925 Å^3
• Polar Surface Area: 53.99 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M294145

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)