Glycosyl phosphates glycoside synthesis

C-Glycosidic linkages are present in various natural products and may inhibit glycosidases due to the structural analogy to their O-counterparts.42 Glycosyl phosphates 63 and 48 served successfully in the a-selective synthesis of aryl... 

Scheme 6.12 Rearrangement to C-aryl glycosides from aryl O-glycosides following a-selective synthesis using glycosyl phosphates.

The utility of glycosyl phosphates in the synthesis of C-glycosides was demonstrated in the synthesis of the natural product 8,10-di-O-methyIbergenin 39. Utilizing the O-to-C rearrangement, the key C-aryl linkage was installed and further elaboration afforded the product in good yield. 

Fraser-Reid et al. [21,22] reported the synthesis of polymer supported oligosaccharides using n-pentenyl glycosides, while Seeberger et al. [23] accomplished the synAesis of p-(l- 4)- and p.(2 6)-linked ohgosaccharides using glycosyl phosphates combined with an octenediol linker. 

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