ABSTRACT
1-iodo glycals are valuable intermediates for the synthesis of various C-glycosyl compounds using transition-metal catalyzed cross-coupling reactions such as Sonogashira, Stille, and Suzuki reaction or ortho-C–H activation. Preparation and the utilization of 1-iodo-3,4,6-tri-O-TIPS-d-glucal and 1-iodo-3,4,6-tri-O-TIPS-d-galactal were already published,5,6 but some inconveniences continue to exist in their synthesis. This chapter presents an optimized one-pot synthesis of two new 1-iodo glycals, 3 and 4, starting from easily accessible silylated glycals 1 and 2, respectively. For the isolation of 3 and 4 in the purity sufficient for the subsequent cross-coupling reactions, only partition of the reaction mixture between toluene and water is needed, followed by extraction of the organic layer with sodium thiosulfate solution. Pure thin-layer chromatography 1-iodo-glycals3 and 4 are obtained in 76% and 87% yields, respectively.
