Synthesis of Oligosaccharides on Solid Support Using Thioglycosides and Pentenyl Glycosides

Synthesis of Oligosaccharides on Solid Support Using Thioglycosides and Pentenyl Glycosides 

Institut fiir Organische Chemie, Johann Wolfgang Goethe-Universitat, Frankfurt am Main, Germany 

Thioglycosides were the first example of an anomeric derivatization that serves the dual role of protection and activation. They were introduced in glycosylation reactions by Ferrier et al. in 1973, who used mercury(II) salts as activator.1 After the development of improved methods of their synthesis and activation, thioglycosides together with trichloroacetimidates are now the most commonly used glycosyl 

Treatment of thioglycosides with /V-bromosuccinimide (NBS) in the presence of diethylaminosulfur trifluoride (DAST) or HF-pyridine complex furnishes glycosyl fluorides.23 These can be activated with AgC104/SnCL in the presence of another 

Thioglycosides have been applied in solid-phase oligosaccharide synthesis by several research groups.29-35 Kahne et al. used them as precursors for the generation of 

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