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

• ChemBase ID: 158980
• Molecular Formular: C21H18Cl2O7
• Molecular Mass: 453.26942
• Monoisotopic Mass: 452.04295828
• SMILES: C1[C@@H]([C@H](OC1OC(=O)C)COC(=O)c1ccc(cc1)Cl)OC(=O)c1ccc(cc1)Cl
• Canonical SMILES: Clc1ccc(cc1)C(=O)OC[C@H]1OC(C[C@@H]1OC(=O)c1ccc(cc1)Cl)OC(=O)C
• InChI: InChI=1S/C21H18Cl2O7/c1-12(24)28-19-10-17(30-21(26)14-4-8-16(23)9-5-14)18(29-19)11-27-20(25)13-2-6-15(22)7-3-13/h2-9,17-19H,10-11H2,1H3/t17-,18+,19?/m0/s1
• InChIKey: XHRJNOXRTTZFEQ-PAMZHZACSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S)-5-(acetyloxy)-3-(4-chlorobenzoyloxy)oxolan-2-yl]methyl 4-chlorobenzoate
• IUPAC Traditional name: [(2R,3S)-5-(acetyloxy)-3-(4-chlorobenzoyloxy)oxolan-2-yl]methyl 4-chlorobenzoate
• Synonyms: 1-Acetate 3,5-Bis(4-chlorobenzoate)-2-deoxy-D-erythro-pentofuranose; 1-O-Acetyl-3,5-bis(4-chlorobenzoyl)-2-deoxy-D-ribose

Database IDs

• CAS Number: 1207459-15-1
• PubChem SID: 162253115
• PubChem CID: 53259161

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 5.2382483
• LogD (pH = 7.4): 5.2382483
• Log P: 5.2382483
• Molar Refractivity: 106.8553 cm^3
• Polarizability: 42.615627 Å^3
• Polar Surface Area: 88.13 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A164255

1-O-Acetyl-3,5-bis(4-chlorobenzoyl)-2-deoxy-D-ribose is an intermediate of Decitabine (5-Aza-2’-deoxy Cytidine) (A796950).

REFERENCES

• Tai-Shun, L., et al.: Tetrahedron, 51, 1055 (1995)
• Gaubert, G., et al.: Eur. J. Med. Chem., 35, 1011 (1995)