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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