Stereoselectivity glycoside linkages

Chemistry of the glycoside linkage. Exceptionally fast and efficient formation of glycosides by remote activation, Carbohydr. Res. 80 07 (1980). (e) K. Wiesner, T. Y. R. Tsai, and H. Jiu, On cardioactive steroids. XVI. Stereoselective P-glycosylation of digitoxose the synthesis of digitoxin, Helv. Chim. Acta 60 300 (1985). (f) R. B. Woodward (and 48 collaborators), Asymmetric total synthesis of erythromycin. 3. Total synthesis of erythromycin, J. Am Chem. Soc. 103 3215 (1981). (g) P. G. M. Wuts and S. S. Bigelow, Total synthesis of oleandrose and the avermecin disaccharide, benzyl ot-L-oleandrosyl-ot-L-4-acetOxyoleandroside, J. Org. Chem. 43 3489 (1983). 

The stereoselective formation of a glycosidic bond is the key feature of oligosaccharide synthesis. Despite the many powerful glycosylation methods that have been developed, there are still a few glycosidic linkages that are difficult to synthesise. For example, the / -mannosidic bond presents a synthetic challenge because the anomeric effect favours the formation of... 

Nagai, H, Matsumura, S, Toshima, K, Environmentally benign and stereoselective formation of p-O-glycosidic linkages using benzyl-protected glucopyranosyl phosphite and montmorillonite K-10, Tetrahedron Lett, 43, 847-850, 2002. 

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