Abstract
Abstract 3-O-Methyl-3-C-trifluoromethyl- d -ribono-(and l -lyxono)-γ-lactones have been prepared from protected d -hexoses (gluco, galacto) by multi-step routes from d -glucose. The synthetic strategy includes the following steps: regioselective oxidation, nucleophilic trifluoromethylation with the Ruppert-Prakash reagent of 3-keto hexofuranose derivatives attacked stereoselectively from the less hindered face, protective group manipulations, and regioselective oxidation of a hemiacetalic hydroxyl. Base-catalyzed hydrolysis of two related d -ribonolactones afforded 3-O-Me-3-C-CF3- d -ribonic acid.
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