A NEW METHOD OF ACETONATION WITH THE ZEOLITE HY AS CATALYST - SYNTHESIS OF O-ISOPROPYLIDENE SUGAR-DERIVATIVES

Citation
Ap. Rauter et al., A NEW METHOD OF ACETONATION WITH THE ZEOLITE HY AS CATALYST - SYNTHESIS OF O-ISOPROPYLIDENE SUGAR-DERIVATIVES, Tetrahedron, 51(23), 1995, pp. 6529-6540
Citations number
27
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
51
Issue
23
Year of publication
1995
Pages
6529 - 6540
Database
ISI
SICI code
0040-4020(1995)51:23<6529:ANMOAW>2.0.ZU;2-F
Abstract
Zeolite HY proved to be a suitable catalyst for the acetonation of sug ars. The method consists of a very simple and economic experimental pr ocedure, in which the catalyst is recovered and can be regenerated Rea ction 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 yi elds from 37-75%. Reaction with D-galactose and L-arabinose afforded t he synthesis of the corresponding furanose derivatives as major produc ts, together with minor quantities of the thermodynamically more stabl e pyranose derivatives.