title: Reductive cleavage of glycosides with borane complexes in the presence of boron trifluoride etherate.
abstract: Mixtures consisting of five equivalents each of borane.methyl sulfide and boron trifluoride etherate per equivalent of acetal or five equivalents of various amine-borane complexes and 10 equivalents of boron trifluoride etherate readily accomplished reductive cleavage of the glycosidic linkages of several per-O-methylated monosaccharides and polysaccharides. In all cases, the expected products were obtained in the expected molar proportions and no artifactual products were observed. Reductive-cleavage analysis using these reagents is particularly convenient because the reagents themselves are easy to handle and because subsequent acetylation of the products is accomplished in situ.
authors.affiliation: Department of Chemistry, University of Minnesota, Minneapolis 55455, USA.
authors.forename: I H
authors.initials: IH
authors.lastname: Oh
authors.forename: G R
authors.initials: GR
authors.lastname: Gray
mesh_terms: D000107:Acetylation; D001880:Boranes / Q000737:chemistry*; D002482:Cellulose / Q000737:chemistry; D005630:Fructans / Q000737:chemistry; D005936:Glucans / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry*; D007444:Inulin / Q000737:chemistry; D007700:Kinetics; D008745:Methylation; D015394:Molecular Structure; D009005:Monosaccharides / Q000032:analysis / Q000737:chemistry*; D010084:Oxidation-Reduction; D011134:Polysaccharides / Q000032:analysis / Q000737:chemistry*; D013395:Sucrose / Q000737:chemistry
chemical_list: D001880:Boranes; D005630:Fructans; D005936:Glucans; D006027:Glycosides; D009005:Monosaccharides; D011134:Polysaccharides; D013395:Sucrose; C021274:boron trifluoride; C009109:pullulan; D002482:Cellulose; D007444:Inulin; C072599:levan