gem-Difluoro-carbasugars, the cases of mannopyranose and galactopyranose
5a-Difluoro-5a-carbamannopyranose (gem-difluoro-carbamannopyranose) and 5a-difluoro-5a-carbagalactopyranose (gem-difluoro-carbagalactopyranose), close congeners of their respective natural sugars, in which the endocyclic oxygen atom has been replaced by a gem-difluoromethylene group, were synthesize...
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Published in: | Carbohydrate research Vol. 342; no. 12-13; pp. 1689 - 1703 |
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Abstract | 5a-Difluoro-5a-carbamannopyranose (gem-difluoro-carbamannopyranose) and 5a-difluoro-5a-carbagalactopyranose (gem-difluoro-carbagalactopyranose), close congeners of their respective natural sugars, in which the endocyclic oxygen atom has been replaced by a gem-difluoromethylene group, were synthesized from d-mannose and d-galactose, using a rearrangement strategy. |
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AbstractList | 5a-Difluoro-5a-carbamannopyranose (gem-difluoro-carbamannopyranose) and 5a-difluoro-5a-carbagalactopyranose (gem-difluoro-carbagalactopyranose), close congeners of their respective natural sugars, in which the endocyclic oxygen atom has been replaced by a gem-difluoromethylene group, were synthesized from d-mannose and d-galactose, using a rearrangement strategy. |
Author | Guieu, Samuel Sinaÿ, Pierre Deleuze, Aurélie Marrot, Jérôme Rauter, Amelia Pilar Jiménez-Barbero, Jesús Sollogoub, Matthieu Fernández-Alonso, M. Carmen Sardinha, João |
Author_xml | – sequence: 1 givenname: João surname: Sardinha fullname: Sardinha, João organization: Université Pierre et Marie Curie-Paris 6, Institut de Chimie Moléculaire (FR 2769), ENS, UMR CNRS 8642, 75005 Paris, France – sequence: 2 givenname: Samuel surname: Guieu fullname: Guieu, Samuel organization: Université Pierre et Marie Curie-Paris 6, Institut de Chimie Moléculaire (FR 2769), ENS, UMR CNRS 8642, 75005 Paris, France – sequence: 3 givenname: Aurélie surname: Deleuze fullname: Deleuze, Aurélie organization: Université Pierre et Marie Curie-Paris 6, Institut de Chimie Moléculaire (FR 2769), ENS, UMR CNRS 8642, 75005 Paris, France – sequence: 4 givenname: M. Carmen surname: Fernández-Alonso fullname: Fernández-Alonso, M. Carmen organization: Departamento de Estructura y Función de Proteínas, Centro de Investigaciones Biológicas, CSIC, Ramiro de Maeztu 9, 28040 Madrid, Spain – sequence: 5 givenname: Amelia Pilar surname: Rauter fullname: Rauter, Amelia Pilar organization: Departamento de Química e Bioquímica, Faculdade de Ciências da Universidade de Lisboa, Edifício C8, 5o Piso, 1749-016 Lisboa, Portugal – sequence: 6 givenname: Pierre surname: Sinaÿ fullname: Sinaÿ, Pierre organization: Université Pierre et Marie Curie-Paris 6, Institut de Chimie Moléculaire (FR 2769), ENS, UMR CNRS 8642, 75005 Paris, France – sequence: 7 givenname: Jérôme surname: Marrot fullname: Marrot, Jérôme organization: Institut Lavoisier, Université de Versailles-Saint-Quentin, 45, Avenue des Etats-Unis, 78035 Versailles Cedex, France – sequence: 8 givenname: Jesús surname: Jiménez-Barbero fullname: Jiménez-Barbero, Jesús organization: Departamento de Estructura y Función de Proteínas, Centro de Investigaciones Biológicas, CSIC, Ramiro de Maeztu 9, 28040 Madrid, Spain – sequence: 9 givenname: Matthieu surname: Sollogoub fullname: Sollogoub, Matthieu email: matthieu.sollogoub@upmc.fr organization: Université Pierre et Marie Curie-Paris 6, Institut de Chimie Moléculaire (FR 2769), ENS, UMR CNRS 8642, 75005 Paris, France |
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SubjectTerms | Carbasugars Carbohydrate Conformation Fluorine Fluorine - chemistry Galactose - analogs & derivatives Galactose - chemistry Indicators and Reagents Inositol Mannose - analogs & derivatives Mannose - chemistry Mimics Models, Molecular |
Title | gem-Difluoro-carbasugars, the cases of mannopyranose and galactopyranose |
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