In this work, the synthetic development of an oxime resin aminolysis to lincosamide analogues is described. This synthetic endeavour hinges on a protecting-group-free strategy of the aminosugar nucleophiles. The cleavage from the solid support is achieved under mild condition in a buffer solution and allows the preparation a wide diversity of amino acid moieties onto glycosylamine scaffolds. The strategy is further exploited using methylthiolincosamine to generate rapidly complex lincomycin analogues. The results pave the way to access efficiently novel potentially relevant antibacterial compounds.
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