194228-75-6Relevant academic research and scientific papers
Synthesis of the First C3 Ribosylated Imidazo[1,2-a]pyridine C-Nucleoside by Enantioselective Construction of the Ribose Moiety
Gudmundsson, Kristjan S.,Drach, John C.,Townsend, Leroy B.
, p. 984 - 989 (1998)
The metabolic instability of the glycosidic linkage in 2,5,6-trichloro-1-(β-D-ribofuranosyl)benzimidazole prompted us to synthesize the structurally related C-nucleoside 2,6,7-trichloro-3-(β-D-ribofuranosyl)imidazor[1,2-α]pyridine. Synthesis of this first C3-ribofuranosylimidazo[1,2-a]pyridine was accomplished by developing a modification of existing iodocyclization methodology for obtaining a 1′,4′-syn furanosyl precursor, without an extensive protection scheme. This 1′,4′-syn precursor was elaborated into the desired ribofuranosyl C-nucleoside. X-ray crystallography was used to unambiguously determine structure and absolute stereochemistry of this C-nucleoside.
