Misc

Highly stereoselective synthesis of 1,2-cis glycosides remains a challenging task due to the lack of reliable neighboring group participation (NGP) from the 2-O-acyl functionality in the glycosyl donor. In this context, our group recently developed highly 1,2-cis-stereoselective glycosylation methods, named boron-mediated aglycon delivery (BMAD), using organoboron reagents and 1,2-anhydroglycosyl donors. In this mini-review article, we introduce the BMAD methods and their applications to the synthesis of biologically active natural products and complex glycosides reported since our mini-review article published in this journal in 2017.

© 2018 FCCA (Forum: Carbohydrates Coming of Age) Development of regio- and stereoselective glycosylations leading to a specific hydroxyl group among several free hydroxyl groups is a challenging and long-standing research subject in carbohydrate chemistry. In this context, several efficient regio- and stereoselective glycosylation methods utilizing organoboron reagents, which can bind reversibly to cis-1,2- or 1,3-diols under mild conditions, have been reported. In this focused review article, several organoboron-mediated regio- and stereoselective glycosylations are described, including recently developed methods.