18604-34-7Relevant academic research and scientific papers
A new method of acetonation with the zeolite HY as catalyst. Synthesis of O-lsopropylidene sugar derivatives
Rauter, Amelia P.,Ramoa-Ribeiro, Fernando,Fernandes, Ana C.,Figueiredo, Jose A.
, p. 6529 - 6540 (2007/10/02)
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.
Application of a phase transfer reaction to the synthesis of L-fructose
Gizaw, Yonas,BeMiller, James N.
, p. 81 - 86 (2007/10/02)
L-Fructose was prepared in five steps from L-sorbose (1). 1,2-O-Isopropylidene-α-L-sorbopyranose (2), prepared from 1, was selectively tosylated using phase transfer catalysis to give 1,2-O-isopropylidene-3-O-(p-tolylsulfonyl)-α-L-sorbopyranose (3).Formation of a 3,4-anhydro ring, followed by its base-catalyzed opening to effect overall inversion of configuration at both C-3 and C-4 gave 1,2-O-isopropylidene-α-L-fructopyranose (5), which was deacetonated to yield L-fructose (6).Keywords: Phase transfer catalysis; Synthesis of L-fructose; Fructose, L-
