Bioorganic & Medicinal Chemistry Letters 2008-06-01

Stereospecific deuteration of alpha-furanosyl azomycin nucleosides: a model reaction for tritium radiolabeling.

Piyush Kumar, Saeed Emami, Alexander J B McEwan, Leonard I Wiebe

Index: Bioorg. Med. Chem. Lett. 18(11) , 3256-60, (2008)

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Abstract

Stereospecific synthesis of 1-alpha-d-(2-deuteroribofuranosyl)-2-nitroimidazole (2'-[(2)H]-alpha-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.