Glycosyl sulfoxides, synthesis

SCHEME 3.15 Synthesis of disaccharide 33 using glycosyl sulfoxide. Piv, pivaloyl. 

Crich and co-workers have demonstrated elegantly that the stereoselective synthesis of fi-mannosides with glycosyl sulfoxides proceeds via anomeric a-triflate intermediates (51). Crich... 

In a different version of the same concept. Stork [67,68] and Bols [69-72] introduced silylene type tethering with glycosyl sulfoxide [67,68] or thioglycoside [69-72] donors. The silicon-tethered acceptor approach was also extended to the synthesis of a-D-gluco- [70,72] and a-D-galactopyranosyl linkages in oligosaccharides [70,72]. 

Scheme 8 Solid phase synthesis of a trisaccharide by the glycosyl sulfoxide method.

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