Glucose dithioacetals, hydrolysis

On the other hand, diacetone D-glucose was transformed to (-)- and (+)-sesbanimide A via the open chain derivative 3-0-benzyl-D-glucose diethyldithioacetal 17, which was prepared by hydrolysis of 3-C -benzyl-l,2 5,6-di-C -isopropylidene-D-glucofuranose (16) and subsequent treatment with ethanethiol in the presence of acid (Scheme 3)4 Acetonation of 17 under kinetic control followed by methylenation with dibromomethane afforded the key intermediate 1,3-dioxane 18. Deprotection of the dithioacetal unit in 18 followed by... 

With Acid. The acid hydrolysis of monothioacetals and dithioacetals has been studied with various thio sugars. Wolfrom et al. [116] studied the hydrolysis of the monothioacetals and dithioacetals (36, a, b) ofZ)-galactoseandZ)-glucose. Using 0.05% hydrochloric acid at 25° the Z)-glucose derivative of (36a) was... 

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