Abstract
Metallation of 5-ethynyl-1-(2,3,5-tri-O,tert-butyldimethylsilyl-β-D-ribofuranosyl)imidazole-4-carboxamide (1) using n-BuLi, deuteration with deuterium oxide and removal of the tert-butyldimethylsilyl protecting groups using tetrabutylammonium fluoride yielded [2- 2 H]-5-ethynyl-1-(β-D-ribofuranosyl)imidazole-4-carboxamide (5a, 75 atom % deuterium). Regiospecific deprotection of the masked aldehyde N,N'-diphenylethylenediamino synthon 14 using DIAION PK212 ion-exchange resin (H + form) yielded the aldehyde derivative (15). Reduction of the aldehyde moiety of 15 using excess [ 3 H]NaBH 4 gave the carbinol product 17. Removal of the ribofuranosyl 2,3-isopropylidene protecting group from 17 using 90% trifluoroacetic acid afforded 5-ethynyl-1-([5- 3 H]-β-D-ribofuranosyl)imidazole-4-carboxamide (18, 19% chemical yield, > 99% radiochemical purity, specific activity 1.56 Ci/mmol).
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