2,3,4-Tri-O-Benzoyl-6-O-(Tert-Butyldiphenylsilyl)-1-Thio-β-d-Glucopyranose

Abstract

Glycosyl thiol derivatives are valuable building blocks in carbohydrate chemistry. In contrast to their hemiacetal counterpart, they display excellent stability toward mutarotation, which allows stereocontrol of the C-1 configuration. 1-Thio derivatives may be used in the synthesis of biologically relevant molecules, such as glycosyl sulfenamides/sulfonamides, glycosyl disulfides, glycosyl thionolactones, and also thiosaccharides known to be resistant toward glycosidase-mediated bond cleavage. In 2013, Misra et al. described a new method to form stereospecifically s-glycosyl thiols from corresponding a-glycosyl bromides upon treatment with disodium sulfide nonahydrate and carbon disulfide in excellent yields. Levoglucosan was purchased from Carbosynth and used without further purification. Reactions requiring dry conditions were carried out in flame-dried glassware and under positive pressure of nitrogen. Analytical Thin Layer Chromatography (TLC) was performed on silica gel plates (GF 254 Merck).