Natural Product Synthesis & Chemical Biology

1.Regio- and stereo-selective synthesis of aryl 2-deoxy-C-glycopyranosides by palladium-catalyzed...

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The Heck coupling of aryl iodides with pyranoid glycals using a catalytic amount of Pd(OAc)2 to form pyranoid aryl C-glycosides has been achieved. The reaction takes place smoothly in the presence of Ag2CO3 and Cu(OAc)2 (or DMSO) in acetonitrile. This arylation process, which occurs in a highly regio- and stereo-selective manner, provides a simple, mild, and efficient approach to the synthesis of aryl 2-deoxy-C-glycopyranosides.

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