Stereospecific deuteration of α-furanosyl azomycin nucleosides: A model reaction for tritium radiolabeling

Stereospecific synthesis of 1-α-d-(2-deuteroribofuranosyl)-2-nitroimidazole (2′-[2H]-α-AZR) is reported. This, deuteration was independent of the configuration of C-2′ –OH group (arabinose or ribose) in sugar moiety of starting molecules. Slightly better yield (>37%) of the deuterated product, 6, from arabinosyl precursor in comparison to corresponding ribose precursor (29%) was obtained which may reflect better stereochemical availability of C-2′ –OH in arabinose during oxidation.

Graphical abstractStereospecific synthesis of 1-α-d-(2′-deuteroribofuranosyl)-2-nitroimidazole 7 starting from 1-α-d-(3′,5′-O,O-tetraisopropyldisilyloxyribo/arabinofuranosyl)-2-nitroimidazole (2 and 4) is reported. This isotopic deuteration was independent of the configuration of –OH group at C-2′ position of sugar moiety in the parent molecules.Figure optionsDownload full-size imageDownload as PowerPoint slide