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Now showing items 11-20 of 36
Synthesis of α-galactosyl ceramide analogues with an α-triazole at the anomeric carbon
(Elsevier, 2014-03-16)
The synthesis of 1,2,3-triazole containing analogues of a-GalCer and galacturonic acid containing Sphingomonous cell wall antigens is described. Anomerisation was used to provide the required cc-glycosyl azide precursor. ...
Combining glycocluster synthesis with protein engineering: an approach to probe into the significance of linker length in a tandem-repeat-type lectin (galectin-4)
(Elsevier, 2014-05-07)
Complementarity in lectin-glycan interactions in situ is assumed to involve spatial features in both the lectin and the glycan, giving a functional meaning to structural aspects of the lectin beyond its carbohydrate-binding ...
Decorated macrocycles via ring-closing double-reductive amination. Identification of an apoptosis inducer of leukemic cells that at least partially antagonizes a 5-HT2 receptor
(American Chemical Society, 2015-03-16)
A build-couple-pair strategy, including double-reductive amination macrocyclization, has been used to generate decorated macrocycles (eannaphanes) with an embedded triazole and monosaccharide. Biological screening led to ...
Methyl 2,3,6-tri-O-Benzoyl-4-O-(tert-butyldimethylsilyl)-β-d-galactopyranoside
(MDPI (Multidisciplinary Digital Publishing Institute), 2017-03-19)
Methyl 2,3,6-tri-O-benzoyl-4-O-(tert-butyldimethylsilyl)-β-d-galactopyranoside was synthesized in 47% yield by the silylation of a partially benzoylated galactose derivative, prepared from methyl β-d-galactopyranoside. ...
Allylic azide rearrangement in tandem with intramolecular Huisgen cycloaddition for iminosugar and glycomimetic synthesis. Functionalized piperidine, pyrrolidine and pyrrolotriazoles from D-mannose
(Thieme Publishing, 2017-04-20)
Intramolecular Huisgen azide-alkene cycloaddition reaction of 7-azido-hepta-1,5-diene-3,4-diols, prepared from methyl α-d-mannopyranoside, were carried out. Allylic azide rearrangement to secondary azides occurred ...
Stereoselective epimerizations of glycosyl thiols
(American Chemical Society, 2017-10-17)
Glycosyl thiols are widely used in stereoselective S-glycoside synthesis. Their epimerization from 1,2-trans to 1,2-cis thiols (e.g., equatorial to axial epimerization in thioglucopyranose) was attained using TiCl4, while ...
SnCl4- and TiCl4-catalyzed anomerization of acylated O- and S-Glycosides: analysis of factors that lead to higher alpha:beta anomer ratios and reaction rates
(American Chemical Society, 2010-09-13)
The quantification of factors that influence both rates and stereoselectivity of anomerization reactions catalyzed by SnCl4 and TiCl4 and how this has informed the synthesis of alpha-O- and alpha-S-glycolipids is discussed ...
Synthesis of migrastatin analogues as inhibitors of tumour cell migration: exploring structural change in and on the macrocyclic ring
(Wiley, 2015-11-04)
Migrastatin and isomigrastatin analogues have been synthesised in order to contribute to structure-activity studies on tumour cell migration inhibitors. These include macrocycles varying in ring size, functionality and ...
Lectins: getting familiar with translators of the sugar code
(MDPI, 2015-01-22)
The view on the significance of the presence of glycans in glycoconjugates is undergoing a paradigmatic change. Initially mostly considered to be rather inert and passive, the concept of the sugar code identifies glycans ...
Regiospecific anomerisation of acylated glycosyl azides and benzoylated disaccharides by using TiCl4.
(Wiley, 2013-10-25)
Chelation induced anomerisation is promoted when Lewis acids, such as TiCl4 or SnCl4 , coordinate to the pyranose ring oxygen atom and another site, giving rise to endocyclic cleavage and isomerisation to the more stable ...