Collect. Czech. Chem. Commun.
2005, 70, 1411-1428
https://doi.org/10.1135/cccc20051411
Stereoselective Preparation of Precursors of α-C-(1→3)-Disaccharides
Petr Štěpáneka, Ondřej Víchb, Lukáš Wernerb, Ladislav Kniežob,*, Hana Dvořákovác and Pavel Vojtíšekd
a Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo nám. 2, 166 10 Prague 6, Czech Republic
b Department of Chemistry of Natural Compounds, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
c NMR Laboratory, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
d Department of Inorganic Chemistry, Charles University, 128 40 Prague 2, Czech Republic
Abstract
The stereoselectivity of cycloaddition of sugar-containing substituted 1-(thiazol-2-yl)but-2-en-1-ones 1 and vinyl ethers was studied using the achiral vinyl ether/chiral catalyst as well as the chiral vinyl ether/achiral catalyst combinations. It has been shown that Eu(fod)3-catalyzed cycloaddition of oxadienes 1a-1e with the chiral vinyl ethers 9 and 10 affords stereoselectively almost pure cycloadducts 11a-11e and 12a-12e, respectively. The obtained cycloadducts are suitable precursors for the synthesis of α-C-(1→3)-disaccharides, containing 2-deoxy-arabino-hexopyranose moiety of D- or L-configuration.
Keywords: Hetero-Diels-Alder reactions; Cycloadditions; Saccharides; Carbohydrates; Disaccharides; Carba-analogues; Stereoselective synthesis; X-Ray diffraction; Thiazoles; Dihydropyrans; C-Glycosides.
References: 28 live references.
