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

• ChemBase ID: 159510
• Molecular Formular: C28H21Cl3O9
• Molecular Mass: 607.81994
• Monoisotopic Mass: 606.02511529
• SMILES: [C@@H]1(OC(=O)c2ccc(cc2)Cl)[C@@H](COC(=O)c2ccc(cc2)Cl)O[C@H]([C@@H]1OC(=O)c1ccc(cc1)Cl)OC(=O)C
• Canonical SMILES: Clc1ccc(cc1)C(=O)O[C@@H]1[C@@H](COC(=O)c2ccc(cc2)Cl)O[C@H]([C@@H]1OC(=O)c1ccc(cc1)Cl)OC(=O)C
• InChI: InChI=1S/C28H21Cl3O9/c1-15(32)37-28-24(40-27(35)18-6-12-21(31)13-7-18)23(39-26(34)17-4-10-20(30)11-5-17)22(38-28)14-36-25(33)16-2-8-19(29)9-3-16/h2-13,22-24,28H,14H2,1H3/t22-,23-,24-,28-/m1/s1
• InChIKey: PWENFUAUZHQOQD-CBUXHAPBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R,4R,5R)-2-(acetyloxy)-4-(4-chlorobenzoyloxy)-5-[(4-chlorobenzoyloxy)methyl]oxolan-3-yl 4-chlorobenzoate
• IUPAC Traditional name: (2S,3R,4R,5R)-2-(acetyloxy)-4-(4-chlorobenzoyloxy)-5-[(4-chlorobenzoyloxy)methyl]oxolan-3-yl 4-chlorobenzoate
• Synonyms: β-D-Ribofuranose 1-Acetate 2,3,5-Tris(4-chlorobenzoate); 1-O-Acetyl 2,3,5-Tri-O-p-chlorobenzoyl-β-D-ribofuranoside

Database IDs

• CAS Number: 144084-01-5
• PubChem SID: 162253645
• PubChem CID: 10416267

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 7.4369545
• LogD (pH = 7.4): 7.4369545
• Log P: 7.4369545
• Molar Refractivity: 142.9928 cm^3
• Polarizability: 56.72469 Å^3
• Polar Surface Area: 114.43 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 142-143°C

DETAILS

Toronto Research Chemicals - A189525

Used in the synthesis of Clitocine.

REFERENCES

• Moss, R., et al.: J. Med. Chem., 31, 786 (1988)