Stereoselective Total Synthesis of Tri- and Tetrahexoside Wheat Flour Ceramide

Abstract

The wheat glycosphingolipids, O-(β-D-mannopyranosyl-[(1→4)-O-(β-D-mannopyranosyl)]_n-O-(β-D-glucopyranosyl)-(1→1)-(2S, 3S, 4R)-4-hydroxy-N-tetracosanoylsphinganine (n=1 and 2), were stereoselectively synthesized. Silver silicate promoted glycosylation when 4-O-acetyl-2, 3, 6-tri-O-benzyl-α-D-mannopyranosyl bromide was used for elongating the glycan chains, which were latter coupled with the ceramide derivative by the trichloroacetimidate method.