Abstract
O-Isopropenyl glycosides bearing ester protecting groups are activated as glycosyl donors by a variety of electrophiles. Diastereomerically pure β-glycoside products are formed in good yields. Selective activation of O-isopropenyl 2,3,4,6-tetra- O-pivaloyl-β-glucopyranoside in the presence of O-pent-4-enyl 2,3,4,6-tetra- O-benzyl-β-glucopyranoside allows two successive glycosyl couplings to be performed in a single pot to give trisaccharide in 25% yield.
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