Synthesis of a Sialic Acid Containing Complex‐Type N‐Glycan on a Solid Support

Abstract

On solid ground: A new solid-phase synthesis of N-linked glycans featuring 1) highly stereoselective β-mannosylation and microfluidic α-sialylation and 2) efficient glycosylation of the N-phenyltrifluoroacetimidate units on JandaJel resin is reported. Reagent concentration effects by a fluorous solvent are effectively applied, and the use of these methods results in the first synthesis of a sialic acid containing complex-type N-glycan on a solid support. A new solid-phase synthesis of N-linked glycans featuring 1) highly stereoselective β-mannosylation and microfluidic α-sialylation and 2) efficient glycosylation of the N-phenyltrifluoroacetimidate units on JandaJel resin is reported. Reagent concentration effects by a fluorous solvent are effectively applied, and the use of these methods results in the first synthesis of a sialic acid containing complex-type N-glycan on a solid support.