Unprecedented 3-O-methyl-3-C-trifluoromethyl-d-ribono- (and l-lyxono)-γ-lactones synthesized by nucleophilic trifluoromethylation of d-hexose-derived cyclic ketones

• Preparation of 3-CF3 glyconolactones by multi-step routes from d-glucose.
• The introduction of CF3 group was achieved by nucleophilic trifluoromethylation.
• The nucleophilic trifluoromethylation carried out by using Ruppert-Prakash reagent.

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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