A useful strategy for synthesis of the disaccharide of OSW-1

Abstract

A flexible, efficient, and practical synthesis route was developed to synthesize an OSW-1 disaccharide. The synthesis took 13 steps from L-arabinose and D-xylose derivatives, and the overall yield was 7.2%. The region preferentially protects various D-xylose hydroxides because the TBS group selectively reacts with this hydroxide at low concentrations due to greater activity at the C-4 hydroxyl of D-xylose. Then, high efficiency selectively protects C-2 hydroxyl and C-3 hydroxyl of D-xylose, respectively. The first high yield of glycosylation on an OSW-1 synthesis disaccharide was achieved by taking sulfide donor 4 with β-PMP anomeric L-arabinose acceptor 12. The cytotoxicity reveals that the analogy has a high IC50 for a variety of cell types. This approach should provide a versatile way to modify OSW-1's disaccharide.