کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1313581 | 1499314 | 2016 | 4 صفحه PDF | دانلود رایگان |
• 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.
Figure optionsDownload as PowerPoint slide
Journal: Journal of Fluorine Chemistry - Volume 186, June 2016, Pages 111–114