Collect. Czech. Chem. Commun.
2008, 73, 690-700
https://doi.org/10.1135/cccc20080690
Stereoselective Preparation of 2,3-Dideoxy-3-C-[(α-D-galactopyranosyl)methyl]-D-arabino-hexopyranose and 2,3-Dideoxy-3-C-[(α-D-galactopyranosyl)methyl]-L-arabino-hexopyranose
Kamil Parkana, Ondřej Vícha, Hana Dvořákováb and Ladislav Kniežoa,*
a Department of Chemistry of Natural Compounds, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
b NMR Laboratory, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
Abstract
The diastereomeric substituted 2H-dihydropyran derivatives 2b and 3b were obtained by the stereoselective cycloaddition of (E)-4-(tetra-O-benzyl-α-D-galactopyranosyl)-1-(thiazol-2-yl)but-2-en-1-one (1) with either of the enantiomeric chiral vinyl ethers (R)-4 or (S)-4. Reduction of the ester group, transformation of the thiazole ring into an aldehyde group and reaction with an excess of borane afforded the final C-(1→3)-disaccharide structures. The obtained C-(1→3)-disaccharides, containing an L- or D-deoxy-arabino-hexopyranose moiety at the reducing end, were characterized as peracetylated methyl glycosides 9a, 9b and 12a, 12b.
Keywords: C-Disaccharides; Stereoselective synthesis; Saccharide chemistry.
References: 10 live references.
