Tunable Approach to C-Linked Analogs of Glycosamines
| Autor: | Tuniyazi Abuduaini, Sizhe Li, Vincent Roy, Luigi A. Agrofoglio, Olivier R. Martin, Cyril Nicolas |
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| Přispěvatelé: | Institut de Chimie Organique et Analytique (ICOA), Commissariat à l'énergie atomique et aux énergies alternatives (CEA)-Université d'Orléans (UO)-Institut National de la Santé et de la Recherche Médicale (INSERM)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), NICOLAS, Cyril |
| Rok vydání: | 2022 |
| Předmět: | |
| Zdroj: | Journal of Organic Chemistry Journal of Organic Chemistry, In press, ⟨10.1021/acs.joc.2c01650⟩ |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.2c01650⟩ |
| Popis: | International audience; The synthesis of (1R)-2-amino-2-deoxy-β-L-gulopyranosyl benzene, and the α and β form of 2-amino-2-deoxy-Lidopyranosyl benzene derivatives was accomplished through stereospecific addition of tributylstannyllithium to readily available (SR)-or (SS)-N-tert-butanesulfinyl-arabinofuranosylamine building blocks, followed by stereoretentive Pd-catalyzed Migita-Kosugi-Stille cross-coupling, stereoselective reduction and an activation-cyclization strategy. Application of this methodology paves the way to new three-dimensional chemical space and preparation of unknown (non-natural) and complex 2-amino-2-deoxy sugars of biological interest. |
| Databáze: | OpenAIRE |
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