Tunable Approach to C‑Linked Analogs of Glycosamines

The
synthesis of (1R)-2-amino-2-deoxy-β-l-gulopyranosyl benzene and the α and β forms of
2-amino-2-deoxy-l-idopyranosyl 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.