Stereospecific deuteration of alpha-furanosyl azomycin nucleosides: a model reaction for tritium radiolabeling.
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.
Kumar
Piyush
P
Department of Oncologic Imaging, Cross Cancer Institute, 11560 University Avenue Edmonton, Alta., Canada. piyushku@cancerboard.ab.ca
Emami
Saeed
S
McEwan
Alexander J B
AJ
Wiebe
Leonard I
LI
D008958:Models, Molecular; D015394:Molecular Structure; D009593:Nitroimidazoles / Q000138:chemical synthesis / Q000737:chemistry; D009705:Nucleosides / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014316:Tritium
D009593:Nitroimidazoles; D009705:Nucleosides; D014316:Tritium; C006667:azomycin