51224-14-7Relevant articles and documents
PREPARATION OF ANOMERIC PAIRS OF 1-THIOGLYCOSIDES: USE OF ANOMERIZATION CATALYZED BY BORON TRIFLUORIDE
Connolly, Daniel T.,Roseman, Saul,Lee, Yuan C.
, p. 227 - 240 (2007/10/02)
Anomeric pairs of some alkyl 1-thioaldopyranosides of D-galactose, D-glucose, D-mannose, 2-acetamido-2-deoxy-D-glucose, 2-acetamido-2-deoxy-D-galactose, and L-fucose were prepared.The per-O-acetylated, 1,2-trans anomers of 6-(trifluoroacetamido)hexyl 1-thioaldopyranosides and 5-(methoxycarbonyl)pentyl 1-thioaldopyranosides were anomerized with boron trifluoride in dichloromethane.The anomeric mixtures were then separated by chromatography, using columns of either silica gel or an ion-exchange resin.De-blocking of the separated compounds provided pure anomers of 6-aminohexyl 1-thioaldopyranosides or 5-carboxypentyl 1-thioaldopyranosides.The aglycons of the latter glycosides were further extended by reaction with aminoacetaldehyde diethyl acetal, which, after deacetalization of the products, provided an ω-aldehydo group.These series of glycosides could be readily coupled to proteins or solid matrices.