- β-Selective C-arylation of silyl protected 1,6-anhydroglucose with arylalanes: The synthesis of SGLT2 inhibitors
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The stereoselective arylation of hydroxy protected 1,6-anhydro-β-d-glucose with arylalanes to provide β-C-arylglucosides is reported. Modification of triarylalanes, Ar3Al, with strong Br?nsted acids (HX) or AlCl3 produced more reactive arylating agents, Ar2AlX, while the incorporation of alkyl dummy ligands into the arylating agents was also viable. Me3Al and i-Bu2AlH were found useful in the in situ blocking of the C3-hydroxyl group of 2,4-di-O-TBDPS protected 1,6-anhydroglucose. The utility of the method was demonstrated by the synthesis of the SGLT2 inhibitor, canagliflozin.
- Henschke, Julian P.,Wu, Ping-Yu,Lin, Chen-Wei,Chen, Shi-Feng,Chiang, Pei-Chen,Hsiao, Chi-Nung
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p. 2295 - 2309
(2015/09/21)
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- Process for the Preparation of ?-C-Aryl Glucosides
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The present invention provides processes for stereoselectively preparing C-arylglucosides that can be useful as synthetic building block or drugs, including SGLT2 inhibitors.
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