Hectogram‐Scale Synthesis of Saccharosamine

Comprehensive Summary Reports on large‐scale syntheses of rare deoxy sugars are notably limited, which poses a significant obstacle to the identification of glycans containing these rare sugars as potential therapeutic agents in the treatment of infectious diseases. In this manuscript, we present a hectogram‐scale synthesis of the rare 3‐amino sugar, saccharosamine, which is an essential component of the heptadecasaccharide saccharomicins, demonstrating considerable potential for the development of a novel class of antibiotics. The synthesis was initiated from the naturally abundant mannose and involved three batch processes in conjunction with five continuous flow processes, representing the most efficient synthetic pathway established to date. A total of five purification steps were conducted, and the process was meticulously designed to obviate the necessity for column chromatography. The effectiveness of these streamlined procedures, along with straightforward manipulation and purification protocols, effectively addresses the challenges associated with scaling up and provides a viable and environmentally sustainable solution for the rapid synthesis of related rare deoxy sugars.