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Facile Approach to C-Glucosides by Using a Protecting-Group-Free Hiyama Cross-Coupling Reaction: High-Yielding Dapagliflozin Synthesis.
Vanková, Karolína; Rahm, Michal; Choutka, Jan; Pohl, Radek; Parkan, Kamil.
Afiliación
  • Vanková K; Department of Chemistry of Natural Compounds, University of Chemistry and Technology Prague, Technická 5, 166 28, Prague 6, Czech Republic.
  • Rahm M; Department of Chemistry of Natural Compounds, University of Chemistry and Technology Prague, Technická 5, 166 28, Prague 6, Czech Republic.
  • Choutka J; Department of Chemistry of Natural Compounds, University of Chemistry and Technology Prague, Technická 5, 166 28, Prague 6, Czech Republic.
  • Pohl R; Institute of Organic Chemistry and Biochemistry of the Czech Academy of Sciences, Gilead Sciences & IOCB Research Centre, Flemingovo nám. 2, 166 10, Prague, Czech Republic.
  • Parkan K; Department of Chemistry of Natural Compounds, University of Chemistry and Technology Prague, Technická 5, 166 28, Prague 6, Czech Republic.
Chemistry ; 27(41): 10583-10588, 2021 Jul 21.
Article en En | MEDLINE | ID: mdl-34048112
Access to unprotected (hetero)aryl pseudo-C-glucosides via a mild Pd-catalysed Hiyama cross-coupling reaction of protecting-group-free 1-diisopropylsilyl-d-glucal with various (hetero)aryl halides has been developed. In addition, selected unprotected pseudo-C-glucosides were stereoselectively converted into the corresponding α- and ß-C-glucosides, as well as 2-deoxy-ß-C-glucosides. This methodology was applied to the efficient and high-yielding synthesis of dapagliflozin, a medicament used to treat type 2 diabetes mellitus. Finally, the versatility of our methodology was proved by the synthesis of other analogues of dapagliflozin.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Diabetes Mellitus Tipo 2 Límite: Humans Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2021 Tipo del documento: Article País de afiliación: República Checa Pais de publicación: Alemania
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Diabetes Mellitus Tipo 2 Límite: Humans Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2021 Tipo del documento: Article País de afiliación: República Checa Pais de publicación: Alemania