Iron Porphyrin Catalysts Induce Stereospecific Glycosylation with Glycal Epoxides
Hao Xu1, Dakang Zhang1, Xiao-Wen Zhang1
1Department of Chemistry, Brandeis University, 415 South Street, Waltham MA, 02453, United States.
Abstract:
This account highlights an iron porphyrin-catalyzed highly stereospecific glycosylation method for glycal epoxides. This method is effective for a wide variety of previously challenging, hindered secondary sugar acceptors and a broad array of both electron-rich and electron-deficient glycal epoxide donors. It plays a pivot role in stereoselective heparan sulfate oligosaccharide synthesis, and the kinetic studies revealed that this glycosylation proceeds through Sn2-type pathways with both primary and hindered secondary acceptors.
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