Novel stereo controlled glycosylation of 1,2,3,4,6-penta-o-acetyl-β-d-glucopyranoside using MgO–ZrO2 as an environmentally benign catalyst

Glycosylation reactions are most commonly encountered in nature. Synthetically, glycosylations are carried out with Lewis acid catalysts or mineral acids. However an environmental threat associated with catalysts has encouraged process modification by alternative development of solid catalysts based glycosylation reactions, which are commercially viable as well. In this contribution comparative study of glycosidic bond formation of 1,2,3,4,6-penta-o-acetyl-β-d-glucopyranoside with various alcohols over variety of reaction promoters/catalyst like p-toluene sulphonic acid, HCl, H2SO4 and MgO–ZrO2 were taken up to evaluate the performance of this potential promoter/catalysts systems. The best catalyst for the selective synthesis of alkyl-β-d-glucopyranosides was MgO–ZrO2 which remains active upto three runs. This replacement of homogeneous acid catalysts by heterogeneous base catalyst shows alkyl-β-d-glucopyranoside as major product at comparatively low temperature range. The effects of variety of parameters were studied in a batch reactor. The mechanism of the reaction over basic mixed metal oxide at 363 K is put forth.