Facile Approach to C-Glucosides by Using a Protecting-Group-Free Hiyama Cross-Coupling Reaction: High-Yielding Dapagliflozin Synthesis
Jazyk angličtina Země Německo Médium print-electronic
Typ dokumentu časopisecké články
Grantová podpora
A1_FPBT_2021_002
Vysoká Škola Chemicko-technologická v Praze
Gilead Sciences & IOCB Prague Research Centre
PubMed
34048112
DOI
10.1002/chem.202101052
Knihovny.cz E-zdroje
- Klíčová slova
- Hiyama reaction, aryl C-glycosides, cross-coupling, dapagliflozin, protecting-group-free,
- MeSH
- benzhydrylové sloučeniny MeSH
- diabetes mellitus 2. typu * farmakoterapie MeSH
- glukosidy MeSH
- katalýza MeSH
- lidé MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- benzhydrylové sloučeniny MeSH
- dapagliflozin MeSH Prohlížeč
- glukosidy MeSH
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.
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