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Regio- and stereo-selective synthesis of aryl 2-deoxy-C-glycopyranosides by palladium-catalyzed Heck coupling reactions of glycals and aryl iodides

Organic and Biomolecular Chemistry, ISSN: 1477-0520, Vol: 7, Issue: 18, Page: 3855-3861
2009
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The Heck coupling of aryl iodides with pyranoid glycals using a catalytic amount of Pd(OAc) to form pyranoid aryl C-glycosides has been achieved. The reaction takes place smoothly in the presence of Ag CO and Cu(OAc) (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. © 2009 The Royal Society of Chemistry.

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