Abstract: A glycosylation reaction refers to the reaction between a glycosyl donor and glycosyl acceptor to result in a glycoside product. The first step of the reaction is the activation of the glycosyl donor at the anomeric carbon, followed by the reaction of a glycosyl acceptor. New directions are emerging to conduct a glycosylation reaction, in order to achieve an excellent control on anomeric stereoselectivity. A recent example is the Hydrogen-bond-Mediated Aglycone delivery (HAD), in which the reactant having properties of H-bond acceptor tethered with glycosyl donor at the remote carbon (C-3, C-4, C-6) forms H-bonding with a glycosyl acceptor and align it in a proper orientation, that leads to a good stereoselectivity and also accelerates the reaction rate. This presentation focuses on the evolution of Hydrogen-bond-Mediated Aglycone delivery (HAD) and its application to assemble individual sugar moieties to a larger oligosaccharide.


Yasomanee, J. P.; Demchenko, A. V. Am. Chem. Soc. 2012, 134, 20097-20102.

Ito, Y.; Ogawa, T. Chem., Int. Ed. 1994, 33, 1765-1767.

Ishiwata, A.; Lee, Y.; Ito, Y. Biomol. Chem. 2010, 8, 3596-3608.

Yasomanee, J. P.; Demchenko, A. V. Eur. J., 2015, 21, 6572-6581.