- Copper-Catalyzed Anomeric O-Arylation of Carbohydrate Derivatives at Room Temperature
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Direct and practical anomeric O-arylation of sugar lactols with substituted arylboronic acids has been established. Using copper catalysis at room temperature under an air atmosphere, the protocol proved to be general, and a variety of aryl O-glycosides have been prepared in good to excellent yields. Furthermore, this approach was extended successfully to unprotected carbohydrates, including α-mannose, and it was demonstrated here how the interaction between carbohydrates and boronic acids can be combined with copper catalysis to achieve selective anomeric O-arylation.
- Verdelet, Tristan,Benmahdjoub, Sara,Benmerad, Belkacem,Alami, Mouad,Messaoudi, Samir
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p. 9226 - 9238
(2019/08/12)
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- Antagonists of the myelin-associated glycoprotein: A new class of tetrasaccharide mimics
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The tetrasaccharide substructure 1 of the ganglioside GQ1bα shows a remarkable affinity for the myelin-associated glycoprotein (MAG). In the search for structurally simplified and pharmacokinetically improved mimics of 1, biphenyl was identified as a feas
- Schwizer, Daniel,Gaethje, Heiko,Kelm, Soerge,Porro, Michele,Schwardt, Oliver,Ernst, Beat
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p. 4944 - 4957
(2007/10/03)
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- Synthesis of carbohydrate functionalised n-propoxy-Calix[4]arenes
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The Suzuki reaction has been used to couple para-bromophenyl glycosides to boronic acid derivatives of n-propoxy-Calix[4]arene; 'a one-pot' methodology eliminates the need to isolate the boronic acids and increases the overall yield. The synthesis provides a new class of carbohydrate containing calixarenes with a deepened cavity.
- Felix, Caroline,Parrot-Lopez, Helene,Kalchenko, Vitaly,Coleman, Anthony W.
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p. 9171 - 9174
(2007/10/03)
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- Regioselective Bromination of O-β-Glycosylated Aromatics
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The quasi quantitative and regioselective bromination of O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)phenols is described.The orientating effect of the glycoside group is compared with those of other oxygenated groups and its usefulness illustrated with
- Mabic, Stephane,Lepoittevin, Jean-Pierre
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p. 1705 - 1708
(2007/10/02)
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- A New Approach to Carbohydrate Functionalized Aromatic Compounds
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Liquid crystalline aryl-β-O-D-glucosides are synthesized by palladium-catalysed cross-coupling of 4-bromophenyl-β-O-D-tetraacetylglucoside with boronic acids.
- Mueller, Henning,Tschierske, Carsten
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p. 645 - 646
(2007/10/02)
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- Glycosides. Part 1. New Synthesis of 1,2-trans O-Aryl Glycosides, via Tributyltin Phenoxides
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A new method of glycosidation of phenols has been studied.The reaction of tributyltin phenoxides 2 with 1,2,3,4,6-penta-O-acetyl-D-hexopyranosides 3, 7 and 9, in the presence of tin tetrachloride is described.Glycosides 4, 8 and 10 have been isolated in g
- Clerici, Francesca,Gelmi, Maria Luisa,Mottadelli, Sabrina
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p. 985 - 988
(2007/10/02)
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- Novel Synthesis of Aryl 2,3,4,6-Tetra-O-acetyl-D-glucopyranosides
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The glucosidation of phenols with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl fluoride in the presence of BF3*OEt2 to give, predominantly, α-anomers has been studied.In the presence of an amine base, 1,1,3,3-tetramethylguanidine, however, enhanced β-selectivity was achieved.The former reaction provides a novel and useful synthesis of aryl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside whilst the latter is effective for the glycosidation of relatively hindered phenols.
- Yamaguchi, Masahiko,Horiguchi, Akira,Fukuda, Akira,Minami, Toru
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p. 1079 - 1082
(2007/10/02)
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