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Synthesis of (1→3) Thiodisaccharides of GlcNAc and the Serendipitous Formation of 2,3-Dideoxy-(1→2)-thiodisaccharides through a Vinyl Azide Intermediate
(American Chemical Society, 2020-01)
The syntheses of β-S-GlcA(1→3)GlcNAc and β-S-Gal(1→3)GlcNAc thiodisaccharides, which can be considered mimetics of the repeating units of hyaluronan and keratan respectively, were achieved by SN2 displacement of a triflate ...
Synthesis of (1→3) Thiodisaccharides of GlcNAc and the Serendipitous Formation of 2,3-Dideoxy-(1→2)-thiodisaccharides through a Vinyl Azide Intermediate
(American Chemical Society, 2019-12)
The syntheses of β-S-GlcA(1→3)GlcNAc and β-S-Gal(1→3)GlcNAc thiodisaccharides, which can be considered mimetics of the repeating units of hyaluronan and keratan respectively, were achieved by SN2 displacement of a triflate ...
Synthesis of Thiodisaccharide Sulfoxides and Sulfones – Determination of the Configuration of the Sulfur Stereocentre
(Wiley VCH Verlag, 2013-11)
The oxidation of per-O-acetyl (1,3)- and (1,4)-linked thiodisaccharides containing glucose, gulose and galactose residues, with an excess of m-chloroperbenzoic acid afforded the corresponding sulfoxides or sulfones. The ...
Design and Synthesis of 2-Acetamido-2,3-dideoxythiodisaccharides via Diastereoselective Conjugate Addition to Sugar Enone O-Acetyl Oximes. Galactosidase Inhibition Studies
(American Chemical Society, 2018-10)
The key step in a new synthesis of 2-acetamido-2,3-dideoxy-(14)-thiodisaccharides was the conjugate addition of a 1-thiogalactose derivative to E and Z acetyl oximes derived from sugar enones. This reaction was shown to ...
Synthesis of Thiodisaccharides Bearing N-Acetylhexosamine Residues: Challenges, Achievements and Perspectives
(John Wiley & Sons Inc., 2021-06)
Carbohydrate-protein interactions are involved in a myriad of biological processes. Thus, glycomimetics have arisen as one of the most promising synthetic targets to that end. Within the broad variety of glycomimetics, ...
Internal asymmetric induction by the C-6 substituent on the oxidation reaction of interglycosidic sulfur atom of thiodisaccharides
(Royal Society of Chemistry, 2017-09)
Since the enantio or diastereoselective preparation of sulfoxides is a current challenge, we explore the possibility of inducing diastereoselectivity in the oxidation of the sulfur atom of thiodisaccharides, according to ...
Synthesis of galactofuranosyl-(1 → 5)-thiodisaccharide glycomimetics as inhibitors of a β-D-galactofuranosidase
(Royal Society of Chemistry, 2015-05)
The first synthesis of methyl β-D-galactofuranosyl-(1 → 5)-thiofuranosides is reported. These molecules, which have the 6-deoxy-5-thio derivative of L-altrofuranose (16) or D-galactofuranose (18) as the reducing end, are ...
Thiodisaccharide sulfoxides: Absolute configuration of the so sulfur atom and influence on the biological activity towards the β-galactosidase from E. coli
(Wiley VCH Verlag, 2015-02)
Benzyl 3-deoxy-4-S-(β-D-galactopyranosyl)-4-thio-β-D-threopentopyranoside (3) is a potent inhibitor of the β-galactosidase from Escherichia coli synthesized in our laboratory. The 2′,3′,4′,6′-tetra-O-acetyl derivative of ...
Synthesis of the (1→6)-linked thiodisaccharide of galactofuranose. Inhibitory activity against a β-galactofuranosidase
(Elsevier, 2013-06-01)
Methyl (methyl alpha,beta-D-galactofuranosid)uronate was employed as the starting compound,which was per-O-silylated with TBSCl and reduced with LiAlH4 to afford methyl 2,3,5-tri-O-tert-butyldimethylsilyl-b-D-galactofuranoside ...
Synthesis and biological activity of divalent ligands based on 3-deoxy-4-thiolactose, an isosteric analogue of lactose
(Royal Society of Chemistry, 2013)