A new method of acetonation with the zeolite HY as catalyst. Synthesis of O-lsopropylidene sugar derivatives

Article abstract of DOI:10.1016/0040-4020(95)00291-F

Zeolite HY proved to be a suitable catalyst for the acetonation of sugars. The method consists of a very simple and economic experimental procedure, in which the catalyst is recovered and can be regenerated. Reaction with D-galactose, L-arabinose, D-glucose, D-xylose, L-sorbose, D-glucofuranurono-6,3-lactone, D-ribose and its methyl glycoside led to the formation of di-O- and/or mono-O-isopropylidene derivatives in yields from 37-75%. Reaction with D-galactose and L-arabinose afforded the synthesis of the corresponding furanose derivatives as major products, together with minor quantities of the thermodynamically more stable pyranose derivatives. Acetonation of D-glucose, D-galactose, L-arabinose, D-xylose, L-sorbose, D-ribose, methyl β-D-ribofuranoside and D-glucofuranurono-6,3-lactone was performed by reaction with acetone using the zeolite HY as catalyst. Synthesis of O-isopropylidene derivatives was accomplished in moderate to good yields (37-75%). The method consists of a very simple and economic experimental procedure, in which the catalyst is recovered and can be regenerated. Reaction with D-galactose and L-arabinose afforded the synthesis of the corresponding di-O-isopropylidene and mono-O-isopropylidene furanose derivatives as major products, together with minor quantities of the thermodynamically more stable pyranose derivatives.