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Synlett 2000; 2000(5): 0734-0736
DOI: 10.1055/s-2000-6609
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Organocopper Reagents (RCu, R2CuLi) for the Nucleophilic C-Glycosylation of a C(2)-Formyl Glycal

Janine Cossy* , Haja Rakotoarisoa
  • *Laboratoire de Chimie Organique, associé au CNRS, ESPCI, 10 rue Vauquelin, 75231 Paris Cedex 05, France
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Publication Date:
31 December 2000 (online)

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C(1)-Glycosides are obtained stereoselectively from C(2)-formyl glycal by nucleophilic addition of alkylcopper reagents (RCu) in the presence of BF3 · OEt2 (SN2′ reaction) or by nucleophilic addition of lithium dialkylcuprates (1,4-addition).

glycals - C-glycosylation - organocopper - SN2′ reaction - 1,4-addition