An approach to stereoselective preparation of 3-C-glycosylated D- and L-glucals.
An approach to stereoselective synthesis of alpha- or beta-3-C-glycosylated L- or D-1,2-glucals starting from the corresponding alpha- or beta-glycopyranosylethanals is described. The key step of the approach is the stereoselective cycloaddition of chiral vinyl ethers derived from both enantiomers of mandelic acid. The preparation of 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)methyl]-L-arabino-hex-1-enitol, 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)methyl]-D-arabino-hex-1-enitol, and 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)methyl]-D-arabino-hex-1-enitol serves as an example of this approach.
Parkan
Kamil
K
Department of Chemistry of Natural Compounds, Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic.
Werner
Lukás
L
Lövyová
Zuzana
Z
Prchalová
Eva
E
Kniezo
Ladislav
L
D004187:Disaccharides / Q000138:chemical synthesis*; D006031:Glycosylation; D008333:Mandelic Acids / Q000737:chemistry; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000737:chemistry
D004187:Disaccharides; D008333:Mandelic Acids; D014753:Vinyl Compounds; C100195:vinyl ether; C037938:mandelic acid