[(2R,3R,5R)-5-chloro-3-(4-chlorobenzoyloxy)oxolan-2-yl]methyl 4-chlorobenzoate

• ChemBase ID: 167036
• Molecular Formular: C19H15Cl3O5
• Molecular Mass: 429.6784
• Monoisotopic Mass: 427.99850662
• SMILES: [C@H]1(C[C@H](O[C@@H]1COC(=O)c1ccc(cc1)Cl)Cl)OC(=O)c1ccc(cc1)Cl
• Canonical SMILES: Clc1ccc(cc1)C(=O)OC[C@H]1O[C@@H](C[C@H]1OC(=O)c1ccc(cc1)Cl)Cl
• InChI: InChI=1S/C19H15Cl3O5/c20-13-5-1-11(2-6-13)18(23)25-10-16-15(9-17(22)26-16)27-19(24)12-3-7-14(21)8-4-12/h1-8,15-17H,9-10H2/t15-,16-,17+/m1/s1
• InChIKey: QEHCZULNFYDPPL-ZACQAIPSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,5R)-5-chloro-3-(4-chlorobenzoyloxy)oxolan-2-yl]methyl 4-chlorobenzoate
• IUPAC Traditional name: [(2R,3R,5R)-5-chloro-3-(4-chlorobenzoyloxy)oxolan-2-yl]methyl 4-chlorobenzoate
• Synonyms: 2-Deoxy-α-D-erythro-pentofuranosyl Chloride 3,5-Bis(4-chlorobenzoate); 1-Chloro-2-deoxy-3,5-O-bis(p-chlorobenzoyl)-α-D-erythro-pentofuranose; 3,5-Bis(4-chlorobenzoyl)-2-deoxy-.alpha.-D-ribofuranosyl Chloride; NSC 140594; 3,5-Di-O-(p-chlorobenzoyl)-2-deoxy-α-D-ribofuranosyl Chloride

Database IDs

• CAS Number: 21740-23-8
• PubChem SID: 162261169
• PubChem CID: 27443695

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 5.990881
• LogD (pH = 7.4): 5.990881
• Log P: 5.990881
• Molar Refractivity: 101.2414 cm^3
• Polarizability: 39.986343 Å^3
• Polar Surface Area: 61.83 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 110-118°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D432235

Intermediate used in the synthesis of nucleotide analogs.Unstable in solution!

REFERENCES

• Sauve, A., et al.: Biochem., 41, 8455 (2002)
• Jain, M., et al.: Bioorg. Med. Chem., 14, 7333 (2002)