32741-93-8Relevant academic research and scientific papers
β-Selective C-Arylation of Diisobutylaluminum Hydride Modified 1,6-Anhydroglucose: Synthesis of Canagliflozin without Recourse to Conventional Protecting Groups
Henschke, Julian P.,Lin, Chen-Wei,Wu, Ping-Yu,Tsao, Wen-Shing,Liao, Jyh-Hsiung,Chiang, Pei-Chen
, p. 5189 - 5195 (2015)
The β-selective phenylation of benzyl and boronate protected 1,6-anhydroglucose and the direct phenylation of unprotected 1,6-anhydroglucose (10), pretreated with i-Bu2AlH, i-Bu3Al, Et3Al, Me3Al, or n-octyl3Al, with triphenylalane or aryl(chloro)alanes is reported. The utility of the unprotected version of the method is demonstrated by the synthesis of the SGLT2 inhibitor, canagliflozin (1a), from commercially available 10 in one C-C bond-forming step. This approach circumvents the need for conventional protecting groups, and therefore no formal protection and deprotection steps are required. (Chemical Presented).
Process for the Preparation of ?-C-Aryl Glucosides
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Paragraph 0282; 0283; 0284, (2014/05/20)
The present invention provides processes for stereoselectively preparing C-arylglucosides that can be useful as synthetic building block or drugs, including SGLT2 inhibitors.
