Stereoselective β‐Mannosylation via Anomeric O‐Alkylation with L‐Sugar‐Derived Electrophiles

Abstract

A total synthesis of the trisaccharide repeat unit of Salmonella serogroup E1 O‐antigen is reported. This synthesis features a key β‐mannosylation reaction through a cesium carbonate‐mediated anomeric O‐alkylation of a partially protected D‐mannose with an L‐fucose‐derived electrophile for the first time.

Synthesis of Glycoconjugates in Potentiating Pharmacological and Pharmaceutical Activity

“…A lack of a variety of glycosyltransferases has been addressed by glycosynthases, which are mutant glycosidases that can easily create glycosidic bonds. The significance of carbohydrate chemistry is emphasised [44,45].…”

Stereoselective Synthesis of β-d-Manno-heptopyranoside via Cs2CO3-Mediated Anomeric O-Alkylation: Synthesis of a Tetrasaccharide Repeat Unit of Bacillus thermoaerophilus Surface-Layer Glycoprotein

“…Nevertheless, the synthesis of 6-deoxy-β- d - manno -heptosides was accomplished via Crich β-mannosylation followed by radical reduction or the use of well-known intramolecular aglycon delivery strategy . In addition, Crich β-mannosylation involving the use of 4,6- O -benzylidene protecting strategy has been applied to the stereoselective synthesis of d - glycero -β- d - manno -heptopyranosides and l - glycero -β- d - manno -heptopyranosides Recently, our group developed an approach for the stereoselective synthesis of β-mannosides involving Cs 2 CO 3 -mediated anomeric O -alkylation , of partially protected mannoses with suitable electrophiles. As part of our program to explore anomeric O -alkylation for microbial glycan synthesis, we became interested in the stereoselective construction of β- d - manno -heptopyranosides.…”