Facile Approach to C-Glucosides by Using a Protecting-Group-Free Hiyama Cross-Coupling Reaction: High-Yielding Dapagliflozin Synthesis

0543667 - ÚOCHB 2022 RIV DE eng J - Článek v odborném periodiku
Vaňková, K. - Rahm, M. - Choutka, J. - Pohl, Radek - Parkan, K.
Facile Approach to C-Glucosides by Using a Protecting-Group-Free Hiyama Cross-Coupling Reaction: High-Yielding Dapagliflozin Synthesis.
Chemistry - A European Journal. Roč. 27, č. 41 (2021), s. 10583-10588. ISSN 0947-6539. E-ISSN 1521-3765
Institucionální podpora: RVO:61388963
Klíčová slova: aryl C-glycosides * cross-coupling * dapagliflozin * Hiyama reaction * protecting-group-free
Obor OECD: Organic chemistry
Impakt faktor: 5.020, rok: 2021
Způsob publikování: Omezený přístup
https://doi.org/10.1002/chem.202101052

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 β-C-glucosides, as well as 2-deoxy-β-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.
Trvalý link: http://hdl.handle.net/11104/0320849