The stereoselective formation of 1, 2-cis-glycosidic bonds is a major bottleneck in the
synthesis of carbohydrates. We here investigate how the electron density in acyl protecting …

Minimal structural differences in the structure of glycosyl donors can have a tremendous
impact on their reactivity and the stereochemical outcome of their glycosylation reactions …

We describe the synthesis of a benzoyl-based C2-O-sLeX-Thr-COOH building block devoid
of any aglycone transfer or orthoester-formed byproducts. The absence of byproducts was …

Uronic acids are carbohydrates carrying a terminal carboxylic acid and have a unique
reactivity in stereoselective glycosylation reactions. Herein, the competing intramolecular …

Sialic acids are monosaccharide residues involved in several biological processes.
Controlling the stereoselectivity of sialylation reactions is challenging and mechanistic …

Abstract The stereoselective formation of 1, 2-cis glycosidic linkages is challenging. The
currently most widely used strategy for their installation uses 4, 6-O-benzylidene-protected …

Nucleophilic substitution reactions of C-2-acyloxy furanosyl acetals can be highly
diastereoselective. We here show that the presence of a less electron-donating p …

Approaching carbohydrate chemistry for the first time can be daunting as basic information is
often buried in texts intended for advanced practitioners in the field. This brief primer …

Using methods of DFT, we investigated the effect of electron withdrawing and electron
donating groups on the relative stability of tentative glycosyl donor reaction intermediates …

Ferrier reactions follow a mechanistic pathway whereby Lewis acid activation of a cyclic enol
ether facilitates departure of an allylic leaving group to form a glycosyl Ferrier cation. Attack …