Oligosaccharide and glycoside synthesis

To date, all TOPCAT donors prepared in our laboratory were isolated by column chromatography as pure (3-anomers (see Scheme 3), and they exhibited much higher stability compared with glycosyl 2-pyridylcarbonates. They are often crystalline and they can be stored for extended periods without a detectable change. These features are extremely important for their synthetic applications as versatile glycosyl donors in oligosaccharide and glycoside synthesis. 

The third theme is concerned with the chemical synthesis of O- and Af-glycosy compounds, and of oligosaccharides, and is the subject of ten chapters. The most widely used methods for glycoside synthesis are discussed, together with the inclusion of concept tually new approaches to anmneric activation and glycoside synthesis. 

Nakano, H., and Kitahata, S. 2005. Application of cyclodextrin glucanotransferases to the synthesis of oligosaccharides and glycosides. In Handbook of Industrial Biocatalysis, ed. C.T. Hon. Boca Raton, FL CRC Press, Taylor Francis Group, pp. 22-1-15. 

Oligosaccharides and Glycosides thereof.—Various steps in the synthesis of benzyl 2-acetamido-4,6-di-0-acetyl-3-0-(2-acetamido-3,4,6-tri-C>-acetyl-2-deoxy- -D-glucopyranosyl)-2-deoxy-a-D-glucopyranoside using a functionalized popcorn polystyrene have been examined. ... 

The Fischer- Helferich method, as a direct anomeric-oxygen replacement reaction (Scheme 1, path A), has been very successfully applied for syntheses of simple alkyl glycosides. However, because of its reversibility, it has not gained general importance in the synthesis of complex oligosaccharides and glycoconjugates (1). 

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