Synthesis of oligosaccharide fragments of the rhamnogalacturonan of Nerium indicum

Abstract

Three trisaccharides, one pentasaccharide, and one heptasaccharide, namely α-D-GalA-(1→2)-α-L-Rha-(1→4)-β-D-GalA-OC3H7 (1), α-L-Rha-(1→4)-α-D-GalA-(1→4)-β-D-GalA-OC3H7 (2), α-D-GalA-(1→4)-α-D-GalA-(1→2)-α-L-Rha-OC3H7 (3), α-D-GalA-(1→2)-α-L-Rha-(1→4)-α-D-GalA-(1→2)-α-L-Rha-(1→4)-β-D-GalA-OC3H7 (4), and α-D-GalA-(1→2)-α-L-Rha-(1→4)-α-D-GalA-(1→2)-α-L-Rha-(1→4)-α-D-GalA-(1→2)-α-L-Rha-(1→4)-β-D-GalA-OC3H7 (5), which are relevant to the fragments of the rhamnogalacturonan of Nerium indicum, were concisely synthesized. The syntheses feature highly stereoselective formation of the α-D-GalA-linkage with GalA N-phenyltrifluoroacetimidates as donors.

Keywords: Glycosyl N-phenyltrifluoroacetimidates; Glycosylation; Nerium indicum; Rhamnogalacturonan; d-Galacturonic acid; l-Rhamnose.