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Diboron-Catalyzed Regio- and 1,2-cis-alpha-Stereoselective Glycosylation of trans-1,2-Diols
Regio- and 1,2-cis-alpha-stereoselective glycosylations were investigated using 1,2-anhydroglucose donors and trans-1,2-diol sugar acceptors in the presence of a diboron catalyst. The reactions proceeded smoothly to provide the corresponding 1,2-cis-alpha-glycosides with consistently very high stereoselectivity and were regioselectivity controlled by the protecting groups of the acceptor. The present glycosylation method was applied successfully to the efficient synthesis of alpha-1,3-glucan pentasaccharide.
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