SnCl 4 Promoted Efficient Cleavage of Acetal/Ketal Groups with the Assistance of Water in CH 2 Cl 2 .

Acetalization and deacetalation are a pair of routine manipulations to protect and deprotect the 4- and 6-hydroxyl groups of glycosides in the synthesis of glycosyl building blocks. In this study, we found that treatment of SnCl 4 with various carbohydrates containing acetal/ketal groups with the assistance of water in CH 2 Cl 2 led to deacetalization/deketalization products in almost quantitative yields. In addition, for substrates containing both acetal/ketal and p -methoxylbenzyl groups, we also found that the p -methoxylbenzyl group was selectively cleaved by the use of a catalytic amount of SnCl 4 , while the acetal/ketal groups remained. Furthermore, based on this, 4,6-benzylidene glycosides can be conveniently converted to 4,6-OAc or 4-OH, 6-OAc glycosides.