Diboron-Catalyzed Regio- and 1,2-<i>cis</i>-α-Stereoselective Glycosylation of <i>trans</i>-1,2-Diols
Shunpei Tomita, Masamichi Tanaka, Michitaka Inoue, Kazuki Inaba, Daisuke Takahashi, Kazunobu Toshima
Abstract
Regio- and 1,2-cis-α-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-α-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 α-1,3-glucan pentasaccharide.
Topics & Concepts
StereoselectivityRegioselectivityGlycosylationChemistryCatalysisDiolStereochemistryAcceptorOrganic chemistryCondensed matter physicsBiochemistryPhysicsCarbohydrate Chemistry and SynthesisGlycosylation and Glycoproteins ResearchEnzyme Production and Characterization