Acetonation of L-pentoses and 6-deoxy-L-hexoses under kinetic control using heterogeneous acid catalysts

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Jonas J. Forsman, Reko Leino
Publisher: ELSEVIER SCI LTD
Publication year: 2010
Journal: Carbohydrate Research
Journal acronym: CARBOHYD RES
Volume number: 345
Issue number: 11
Start page: 1548
End page: 1554
Number of pages: 7
ISSN: 0008-6215
eISSN: 1873-426X


Abstract

The fibrous polymer-supported sulfonic acid catalyst Smopex-101 H(+) proved to be an efficient catalyst for the preparation of O-isopropylidene derivatives from a series of rare sugars. Acetonation of the reducing sugars L-arabinose, L-ribose, L-xylose, L-fucose, and L-rhamnose in N,N-dimethylformamide by 2,2-dimethoxypropane or 2-methoxypropene led to the formation of the kinetically favored di-O- and/or mono-O-isopropylidene derivatives in 46-88% yields. The method consists of a simple experimental procedure which does not require predried solvents or reagents. The catalyst is easily recovered and can be regenerated making the procedure economically viable even for large-scale synthesis.


Keywords

Acetonation, Heterogeneous catalysis, Isopropylidene acetals, Kinetic control, L-Carbohydrates

Last updated on 2019-19-06 at 05:08