Thioglycosides in sequential glycosylation strategies

Abstract

This tutorial review surveys the use of thioglycosides in the development of sequential glycosylation methodologies, with a focus on chemoselective, orthogonal and iterative glycosylation strategies reported since the beginning of this century. Both fundamental aspects of glycosidic bond formation and ingenious state-of-the-art methodologies are presented.

The synthesis and biological evaluation of mycobacterial p-hydroxybenzoic acid derivatives (p-HBADs)

“…Thioglycosides are widely used as glycosyl donors in carbohydrate synthesis due to their relative stability and ability to tolerate functional group modifications on the sugar. 31 Removal of the acetate protecting groups under Zemplén conditions followed by regioselective protection of the 2-and 3-OH groups with a cyclic acetal furnished partially protected donor 4. Benzylation of the free 4-OH followed by hydrolysis of the acetal protecting group furnished the diol 6.…”

Glycosylation Reaction of <i>Thioglycosides</i> by Using Hypervalent Iodine(III) Reagent as an Excellent Promoter

“…Since the first report in 1909, the chemistry of thioglycosides has been significantly investigated and numerous methodologies have been reported on their preparation and activation in the past three decades. [1][2][3][4][5] Thioglycoside donors are relatively easy to prepare, stable under various reaction conditions of protection and deprotection, and offer orthogonality in their activation. 6) An important feature of thioglycosides is their ability to serve not only as glycosyl donors, but also acceptors.…”

Melanoma Cell Factory for Glycolipid Production

“…Sulfur containing compounds have various applications in the pharmaceutical industry and in synthetic chemistry as glycosyl donors for the synthesis of complex oligisaccharides (Castaneda, 2007;Codee, 2005;Garegg, 1997;Krag, 2010;Witzak, 2005). Thiolactosides having a lactose moiety linked to a hydrophobic dodecyl aglycon unit via S-glycosidic bond have also been prepared and administered into mouse melanoma B16 cells (Mori et al, 2011).…”