A metathesis approach for the preparation of polyhydroxylated compounds as head groups in surfactant synthesis

Abstract

Starting from methyl-α-D-glucopyranoside, an efficient protocol for the preparation of polyhydroxylated surfactant head-groups is demonstrated and applied in the synthesis of a typical surfactant. The key transformation is a metathesis reaction between two monosaccharide residues to afford an octahydroxydecen. The importance of a strategic protecting-group constellation for a successful metathesis reaction is also investigated. © Wiley-VCH Verlag GmbH & Co. KGaA, 2006.