Addition of lithiated C-nucleophiles to 2,3-O-isopropylidene-D-erythronolactone: stereoselective formation of a furanose C-disaccharide |
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| Authors: | McCartney Jason L Meta Christopher T Cicchillo Robert M Bernardina Matthew D Wagner Timothy R Norris Peter |
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| Institution: | Department of Chemistry, Youngstown State University, 1 University Plaza, Youngstown, Ohio 44555-3663, USA. |
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| 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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