Synthesis of Fluorinated Homo-C-Nucleoside Analogues from New Carbo­hydrate-Derived Acylsilanes

Abstract

The stereocontrolled synthesis of new carbohydrate-derived acylsilanes with the silylcarbonyl moiety linked to the anomeric carbon via a methylene group is described. Reaction of these acylsilanes with perfluoroorganometallic reagents followed by treatment with hydrazines or amidines led to new polyfluorinated homo-C-nucleoside analogues, in a one-pot or two-step transformation, respectively.

C-Glycopyranosyl aldehydes: emerging chiral synthons in organic synthesis

“…Chanteau et al 99 designed a stereo-controlled synthetic pathway for the synthesis of carbohydrate-derived acylsilanes starting from C -glucopyranosyl aldehyde 4a . The aldehyde 4a undergoes nucleophilic addition on reaction with bis(trimethylsilyl)methoxymethane ( 474 ) in n -butyl lithium–THF via Peterson reaction to furnish enol ether 475 in 49% yield.…”