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9 results on '"Olivier Jarreton"'

2. Samarium Diiodide PromotedC-Glycosylation: An Application to the Stereospecific Synthesis ofα-1,2-C-Mannobioside and Its Derivatives

Author

Jesús Jiménez-Barbero, Olivier Jarreton, Juan-Félix Espinosa, Troels Skrydstrup, and Jean-Marie Beau

Subjects
chemistry.chemical_classification, Glycosylation, Stereochemistry, Radical, Organic Chemistry, chemistry.chemical_element, Glycoside, General Chemistry, Catalysis, Coupling reaction, Samarium, chemistry.chemical_compound, Stereospecificity, chemistry, Yield (chemistry), Carbanion
Abstract

The mannosyl pyridylsulfone 1 undergoes a remarkably efficient coupling reaction with the 2-deoxy-C2-formyl glycoside 2 in the presence of samarium diiodide to provide the corresponding C-disaccharide in high yield. This represents the first step in the synthesis of C-mannobioside, a synthesis which closely resembles approaches employed in O-glycosylation.

Published
1999
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3. Further studies in α-C-mannosylation promoted by samarium diiodide

Author

Troels Skrydstrup, Olivier Jarreton, and Jean-Marie Beau

Subjects
Coupling (electronics), chemistry.chemical_compound, Samarium diiodide, Chemistry, Mannosylation, Organic Chemistry, Drug Discovery, Polymer chemistry, Diastereomer, Cyclohexanone, Nanotechnology, Biochemistry
Abstract

Mannosyl pyridylsulfones with varying C2OH protecting groups were reacted with cyclohexanone in the presence of SmI2. With SiMe2tBu and Bn, high yields of an α-C-mannoside were obtained. In the former case no β-elimination was observed. The relative configuration of the major diastereomer obtained upon coupling with aldehydes was determined.

Published
1997
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4. ChemInform Abstract: The Stereospecific Synthesis of Methyl α-C-Mannobioside: A Potential Inhibitor of M. tuberculosis Binding to Human Macrophages

Author

Jean-Marie Beau, Troels Skrydstrup, and Olivier Jarreton

Subjects
carbohydrates (lipids), chemistry.chemical_compound, Mannobioside, Tuberculosis, Stereospecificity, chemistry, Stereochemistry, medicine, Disaccharide, lipids (amino acids, peptides, and proteins), Glycosyl, General Medicine, medicine.disease
Abstract

The synthesis of the C-glycoside analogue of the mycobacteria capping disaccharide, Manα1–2Man, employing a glycosyl organosamarium is described.

Published
2010
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5. ChemInform Abstract: Further Studies in α-C-Mannosylation Promoted by Samarium Diiodide

Author

Olivier Jarreton, Jean-Marie Beau, and Troels Skrydstrup

Subjects
Coupling (electronics), chemistry.chemical_compound, chemistry, Samarium diiodide, Mannosylation, Diastereomer, Cyclohexanone, General Medicine, Medicinal chemistry
Abstract

Mannosyl pyridylsulfones with varying C2OH protecting groups were reacted with cyclohexanone in the presence of SmI2. With SiMe2tBu and Bn, high yields of an α-C-mannoside were obtained. In the former case no β-elimination was observed. The relative configuration of the major diastereomer obtained upon coupling with aldehydes was determined.

Published
2010
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6. ChemInform Abstract: A General Approach to 1,2-trans-C-Glycosides via Glycosyl Samarium(III) Compounds

Author

Olivier Jarreton, Troels Skrydstrup, Daniel Mazéas, Jean-Marie Beau, and Dominique Urban

Subjects
Samarium, C glycosides, chemistry.chemical_compound, Anomer, chemistry, Stereochemistry, Reagent, chemistry.chemical_element, Stereoselectivity, Glycosyl, Lithium, General Medicine, Coupling reaction
Abstract

A remarkable stereoselective coupling reaction is undergone by glycosyl pyridyl sulfones, such as 1, with carbonyl compounds affording 1,2-trans-C-glycosides. In contrast to the corresponding lithium counterparts the intermediate anomeric organosamarium reagent displays enhanced stability to β elimination of the C2-substituent.

Published
2010
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7. ChemInform Abstract: Samarium Diiodide Promoted C-Glycosylation: An Application to the Stereospecific Synthesis of α-1,2-C-Mannobioside and Its Derivatives

Author

Jesús Jiménez-Barbero, Jean-Marie Beau, Juan-Félix Espinosa, Troels Skrydstrup, and Olivier Jarreton

Subjects
chemistry.chemical_classification, Mannobioside, chemistry.chemical_compound, Glycosylation, Stereospecificity, chemistry, Samarium diiodide, Stereochemistry, Yield (chemistry), Glycoside, General Medicine, Coupling reaction
Abstract

The mannosyl pyridylsulfone 1 undergoes a remarkably efficient coupling reaction with the 2-deoxy-C2-formyl glycoside 2 in the presence of samarium diiodide to provide the corresponding C-disaccharide in high yield. This represents the first step in the synthesis of C-mannobioside, a synthesis which closely resembles approaches employed in O-glycosylation.

Published
2010
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8. A general approach to 1,2-trans-C-glycosides via glycosyl samarium(III) compounds

Author

Dominique Urban, Jean-Marie Beau, Daniel Mazéas, Olivier Jarreton, and Troels Skrydstrup

Subjects
chemistry.chemical_classification, Anomer, Stereochemistry, Organic Chemistry, chemistry.chemical_element, Glycoside, General Chemistry, Catalysis, Coupling reaction, Samarium, chemistry.chemical_compound, chemistry, Reagent, Glycosyl, Stereoselectivity, Carbanion
Abstract

A remarkable stereoselective coupling reaction is undergone by glycosyl pyridyl sulfones, such as 1, with carbonyl compounds affording 1,2-trans-C-glycosides. In contrast to the corresponding lithium counterparts the intermediate anomeric organosamarium reagent displays enhanced stability to β elimination of the C2-substituent.

9. The stereospecific synthesis of methyl α-C-mannobioside: A potential inhibitor of M. tuberculosis binding to human macrophages

Author

Jean-Marie Beau, Olivier Jarreton, and Troels Skrydstrup

Subjects
Mannobioside, Tuberculosis, Stereochemistry, Metals and Alloys, Disaccharide, General Chemistry, medicine.disease, Catalysis, Surfaces, Coatings and Films, Electronic, Optical and Magnetic Materials, carbohydrates (lipids), chemistry.chemical_compound, Stereospecificity, chemistry, Materials Chemistry, Ceramics and Composites, medicine, lipids (amino acids, peptides, and proteins), Glycosyl
Abstract

The synthesis of the C-glycoside analogue of the mycobacteria capping disaccharide, Manα1–2Man, employing a glycosyl organosamarium is described.

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