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Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams.

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.

SUBMITTER: Wieclaw MM

PROVIDER: S-EPMC7814180 | biostudies-literature | 2021

REPOSITORIES: biostudies-literature

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Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams.

Więcław Michał Mateusz MM Furman Bartłomiej B

Beilstein journal of organic chemistry 20210113

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 ...[more]

PMID: 33519998

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