Add time:08/06/2019 Source:sciencedirect.com
An organocopper reagent, derived from allyl(diethylamino)dimethylsilane via metalation by n-BuLi/TMEDA followed by transmetalation, reacts with aldehydes regioselectively at the γ position to form 1-substituted (E)-3-buten-1-ol derivatives. Epoxidation of the double bond followed by hydrogen peroxide cleavage of the carbonsilicon bond affords 2,3-dihydroxy-tetrahydrofuran derivatives, which are further transformed into 2-deoxy-C-nucleoside skeletons via siloxymethylation at the anomeric position. One model system is presented, together with the stereochemical aspects.
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