Solution and Solid-Phase Stereocontrolled Synthesis of 1,2-cis-Glycopyranosides with Minimally Protected Glycopyranosyl Donors Catalyzed by BF3–N,N-Dimethylformamide Complex
作者： Gabrielle St-Pierre , Stephen Hanessian
DOI: 10.1021/ACS.ORGLETT.6B01263
关键词:
摘要: Methods are described for the stereoselective synthesis of 1,2-cis glycopyranosides in d-galacto, d-gluco, and 2-azido-2-deoxy-d-glucopyranoside series utilizing minimally protected (3-bromo-2-pyridyloxy) β-d-glycopyranosyl donors presence BF3–N,N-dimethylformamide (DMF) as a catalyst variety alcohol acceptors relying on “remote activation concept”. Precursors to antifreeze glycopeptide components synthesized excellent yields high α/β ratios. The method is adaptable one-pot sequential glycosidation well solid-supported giving access diverse sets α-d-glycopyranosides major products.
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