Synthesis of 2-deoxy mucin-type O-glycan analogues as biological probes.

Access to mucin-type O-glycans as tools to help further our understanding of the biological role of these complex molecules is of importance. Herein, we report the efficient stereoselective synthesis of four novel 2-deoxyglycoside mucin-type O-glycan analogues. The strategy relies on the use of two common glycoside acceptors bearing a free OH at either C-3 or C-6 and two different orthogonally protected glycal donors, which can be activated using organocatalytic methods or Brønsted acid catalysis in good yields and stereocontrol.

Conformationally Constrained Glycosyl Donors as Tools to Control Glycosylation Outcomes.

The stereoselective synthesis of oligosaccharides remains one of the biggest challenges in carbohydrate chemistry. Many factors, including reaction conditions and the type of glycosyl donor and acceptor used, can affect the outcome of glycosylation reactions. In this Perspective, we discuss methods aimed to control the reactivity and stereoselectivity of glycosylation reactions using conformationally constrained glycosyl donors, with a focus on more recently developed chemistry.