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Glycosyl donors with cyclic silyl protecting groups, such as di-tert-butylsilylene (DTBS) and tetraisopropyldisiloxanylidene (TIPDS) groups, have been found to affect the stereoselectivity of diverse chemical glycosylations. Moreover, the effects of ring-restriction for stereoselective glycosylations have provided new insights into the reaction mechanism of chemical glycosylation. We present a historical overview of stereoselective glycosylations using such ring-restricted glycosyl donors and their applications to the synthesis of biologically relevant carbohydrate molecules.

STEREODIRECTING EFFECT OF CYCLIC SILYL PROTECTING GROUPS IN CHEMICAL GLYCOSYLATION