Stereospecific synthesis of glycoside mimics through Migita-Kosugi-Stille cross-coupling reactions of chemically and configurationally stable 1-C-tributylstannyl iminosugars - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Advanced Synthesis and Catalysis Année : 2020

Stereospecific synthesis of glycoside mimics through Migita-Kosugi-Stille cross-coupling reactions of chemically and configurationally stable 1-C-tributylstannyl iminosugars

Résumé

An innovative and effective strategy for the synthesis of imino-C-glycosides is described. The methodology is based on the unprecedent reaction of 1-C-stannylated iminosugars with various electrophiles under the conditions of Migita-Kosugi-Stille cross-couplings, which gives 1-C-substituted iminosugar derivatives in a stereoretentive process. The required iminoglycosyl stannanes are obtained by way of the highly stereoselective addition of tributylstannyllithium to (SR)-or (SS)-N-tert-butanesulfinyl glycosylamines, followed by an activation cyclization sequence. Most interestingly, the methodology is tunable: the configuration of the tin adduct is controlled exclusively by the tert-butanesulfinyl auxiliary, thus giving access after ring formation to alpha-configured or beta-configured iminoglycosyl stannanes. With the subsequent stereoretentive CC bond-forming process, the methodology allows the synthesis of pseudo anomers of imino-C-glycosyl compounds in a controlled fashion.
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hal-02989536 , version 1 (05-11-2020)

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Sizhe Li, Justyna Jaszczyk, Xavier Pannecoucke, Thomas Poisson, Olivier A.J. Martin, et al.. Stereospecific synthesis of glycoside mimics through Migita-Kosugi-Stille cross-coupling reactions of chemically and configurationally stable 1-C-tributylstannyl iminosugars. Advanced Synthesis and Catalysis, 2020, 363, pp.470-483. ⟨10.1002/adsc.202000886⟩. ⟨hal-02989536⟩
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