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Acetyl-protected 1-(β-d-galactopyranosyl)-2-nitroimidazole was converted to a potential precursor for a fluorine-18 labeled hypoxia tumor marker. Two nonradioactive standards, the 6′-deoxy-6′-fluorogalactosyl and the 4′-deoxy-4′-fluoroglucosyl analogue were also prepared. These 2-nitroimidazole nucleosides were prepared by a modified Vorbrüggen coupling.

3-(Trimethylstannyl)benzyl alcohol was coupled in a Mitsunobu reaction with bis(Boc)-guanidine to give bis(Boc)-protected 3-(trimethylstannyl)benzylguanidine used as precursor for [*I]MIBG. Radioiodination with [131I]iodine generated from [131I]NaI and chloramine-T, removal of Boc groups, and purification by HPLC gave no-carrier-added tracer [*I]MIBG (81% radiochemical yield, 99% chemical purity) used for imaging tumors of neuroendocrine origin. The structures of bis(Boc)-guanidine and bis(Boc)-protected 3-(trimethylstannyl)benzylguanidine were secured by single crystal X-ray structure analyses.