Synthesis and hypolipidemic activity of N-phthalimidomethyl tetra-O-acyl-α-d-mannopyranosides

A facile synthesis of anomerically pure phthalimidomethyl 2,3,4,6-tetra-O-acetyl- and phthalimidomethyl 2,3-di-O-acetyl-4,6-di-O-benzoyl-α-d-mannopyranosides (6 and 9b) starting from N-hydroxymethylphthalimide and tri-O-acetyl-d-glucal is described. Compounds 3, 6, 8, 9a and 9b have been tested for their hypolipidemic activity in mice. All these compound showed significant reduction of plasma cholesterol and triglyceride levels. Compound 9b has been found to possess the highest activity.