Abstract
1-α-and 1-β-D-Arabinofuranosyl-2-nitroimidazole (α-AZA and β-AZA) are synthons for a number of potential markers of tissue hypoxia. A one pot synthesis in which 2-nitroimidazole is coupled with a mixture of α-and β-1-O-acetyl-2,3,5-tri-O-benzoyl-D-arabinofuranose in the presence of stannic chloride, followed by deprotection using ammonia/methanol, is described. Previously reported conditions for coupling 2-nitroimidazole to 1-α-bromoarabinofuranose protected by base-hydrolyzable groups afforded α-AZA almost exclusively.
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