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Article Dans Une Revue Journal of Organic Chemistry Année : 2022

A Tunable Approach to C-Linked Analogs of Glycosamines

Résumé

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.
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Dates et versions

hal-03798583 , version 1 (05-10-2022)

Identifiants

Citer

Tuniyazi Abuduaini, Sizhe Li, Vincent Roy, Luigi A Agrofoglio, Olivier R Martin, et al.. A Tunable Approach to C-Linked Analogs of Glycosamines. Journal of Organic Chemistry, In press, ⟨10.1021/acs.joc.2c01650⟩. ⟨hal-03798583⟩
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