(2S,3S,4R,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-2-methoxyoxolan-3-yl benzoate

• ChemBase ID: 174384
• Molecular Formular: C27H24O8
• Molecular Mass: 476.47466
• Monoisotopic Mass: 476.14711773
• SMILES: [C@H]1([C@H]([C@H]([C@H](O1)OC)OC(=O)c1ccccc1)OC(=O)c1ccccc1)COC(=O)c1ccccc1
• Canonical SMILES: CO[C@H]1O[C@@H]([C@H]([C@H]1OC(=O)c1ccccc1)OC(=O)c1ccccc1)COC(=O)c1ccccc1
• InChI: InChI=1S/C27H24O8/c1-31-27-23(35-26(30)20-15-9-4-10-16-20)22(34-25(29)19-13-7-3-8-14-19)21(33-27)17-32-24(28)18-11-5-2-6-12-18/h2-16,21-23,27H,17H2,1H3/t21-,22-,23+,27+/m1/s1
• InChIKey: XJKNQPQTQXKNOC-LAWREARLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-2-methoxyoxolan-3-yl benzoate
• IUPAC Traditional name: (2S,3S,4R,5R)-4-(benzoyloxy)-5-[(benzoyloxy)methyl]-2-methoxyoxolan-3-yl benzoate
• Synonyms: α-D-Arabinofuranoside Methyl Tribenzoate; Methyl 2,3,5-Tri-O-benzoyl-α-D-arabinoside; Methyl α-D-Arabinofuranoside Tribenzoate; NSC 400281; Methyl 2,3,5-Tri-O-benzoyl-α-D-arabinofuranoside

Database IDs

• CAS Number: 7473-42-9
• PubChem SID: 164230294
• PubChem CID: 11145214

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 5.826822
• LogD (pH = 7.4): 5.826822
• Log P: 5.826822
• Molar Refractivity: 124.1781 cm^3
• Polarizability: 48.991776 Å^3
• Polar Surface Area: 97.36 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform
• Apperance: White Solid
• Melting Point: 98-100°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - M330830

Used in the preparation of 1-α- and 1-β-D-Arabinofuranosyl-2-nitroimidazole (α-AZA and β-AZA) as synthons for a number of potential markers of tissue hypoxia.

REFERENCES

• Vinjamuri, S., et al.: Clin. Nucl. Med., 24, 891 (1999)
• Brown, J., et al.: Mol. Med. Today, 6, 157 (1999)
• Sorger, D., et al.: Nucl. Med. Biol., 30, 317 (1999)