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  • Title: Addition of lithiated C-nucleophiles to 2,3-O-isopropylidene-D-erythronolactone: stereoselective formation of a furanose C-disaccharide.
    Author: McCartney JL, Meta CT, Cicchillo RM, Bernardina MD, Wagner TR, Norris P.
    Journal: J Org Chem; 2003 Dec 26; 68(26):10152-5. PubMed ID: 14682713.
    Abstract:
    Addition of PhLi and lithiated dithianes to 2,3-O-isopropylidene-D-erythronolactone affords lactols, which are reduced with Et3SiH to the corresponding C-glycosides, the structures of two of which have been solved by X-ray diffraction. The use of a d-ribose-derived lithiated dithiane nucleophile in this chemistry allows for the convenient construction of a furanose C-disaccharide.
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