A novel method for the highly stereoselective synthesis of β-(1→2)-C-saccharides employing 3-deoxy- and 3-C-branched glycals as hermaphroditic substrates is revealed. The generality of the C-C bond formation reaction between the two sugar units is evaluated. The developed methodology is successfully applied to the synthesis of biologically significant subunits that are present in various natural products, which include mixed C-disaccharides with adjacent THP-THF rings, C-aryl glycosides, and highly functionalized β-C-glycosides.
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| http://dx.doi.org/10.1021/acs.joc.5b02879 | DOI Listing |
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