Transglucosidation of methyl and ethyl d-glucopyranosides by alcoholysis

Mechanisms of glycopyranosyl and 5-thioglycopyranosyl transfer reactions in solution

“…42 In contrast, acid-catalysed anomerisation of methyl glucofuranosides has been proposed to occur via endocyclic cleavage of the furanose ring to give an acyclic acetal. 42, 43 These mechanistic conclusions were further refined by two recent studies on the acid-catalysed alcoholysis of methyl and ethyl 4-O-methyl-α-and β--glucopyranosides, 44 and of methyl and ethyl 5-O-methyl-α-and β--glucofuranosides. 45 In these two reports, Konradsson and co-workers show that the isomeric glycosides solvolyse by different mechanisms: pyranosides react via a D N ϩ A N exocyclic C-O cleavage, while the At the moment, it appears that the 2-hydroxy group is an important determinant for the mechanism of anomerisation.…”

Sulfonamidoglycosylation of methyl ribofuranosides: a novel approach to furanosylsulfonamides

“…10 Recently Konradsson and co-workers reported on the transglycosidation of methyl glucopyranosides in ethanol or methanol catalyzed by camphorsulfonic acid. 11 Ikegami and co-workers studied the O-transglycosidation of 1-C-methyl hexopyranosides under the influence of several Lewis acids, the best yields were found when SnCl 4 was used as catalyst. 12 1-Phenylselenylfuranosides were prepared by glycosylation of methyl glycosides with PhSeH and boron trifluoride etherate.…”