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Oligosaccharides have valuable effects in biological systems, but their complex nature makes them difficult to convert into chemical tools. We have developed a two-step conversion of unprotected oligosaccharides that is highly amenable to generating a variety of complex oligosaccharide tool compounds. This sequence features an optimized Kochetkov amination procedure and subsequent amide coupling. With these simple synthetic conversions, the creation of novel bioorthogonal carbohydrate probes becomes easily accessible and new avenues for chemical biology may be opened. • Optimized Kochetkov amination procedure for complex oligosaccharides. • Highly versatile amide coupling for facile probe synthesis.