ArticleBeilstein journal of organic chemistry2021
Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams.
Article in Beilstein journal of organic chemistry, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.
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Abstract
Herein we present the direct asymmetric synthesis of tetrazole-functionalized 1-deoxynojirimycin derivatives from simple sugars via a Schwartz's reagent-mediated reductive amide functionalization followed by a variant of the Ugi-azide multicomponent reaction. The anomeric configurations of two products were unambiguously confirmed by X-ray analysis. This work also describes examples of interesting further transformations of the title products. Finally, some surprising observations regarding the mechanism of their formation were made.
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