Synthesis of the Glc3Man N-glycan tetrasaccharide by iterative allyl IAD

The synthesis of the tetrasaccharide α-d-Glcp-(1→2)-α-d-Glcp-(1→3)-α-d-Glcp-(1→3)-α-d-Manp-OMe, corresponding to the terminal tetrasaccharide portion of the glucose terminated arm of the N-glycan tetradecasaccharide, was achieved with complete stereocontrol by the use of iterative allyl protecting group mediated intramolecular aglycon delivery (allyl IAD) demonstrating the utility of intramolecular glycosylation for the stereocontrolled construction of multiple glycosidic linkages during the synthesis of an oligosaccharide.

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