- β-Selective C-Arylation of Diisobutylaluminum Hydride Modified 1,6-Anhydroglucose: Synthesis of Canagliflozin without Recourse to Conventional Protecting Groups
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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).
- Henschke, Julian P.,Lin, Chen-Wei,Wu, Ping-Yu,Tsao, Wen-Shing,Liao, Jyh-Hsiung,Chiang, Pei-Chen
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p. 5189 - 5195
(2015/05/27)
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- Process for production of 2,6-dimethyl-1,3,6-octatriene
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A process for producing 2,6-dimethyl-1,3,6-octatriene by dimerizing isoprene in the presence of a novel catalyst composition, which comprises: (A) a zirconium component represented by the formula: Zr(OR)n Cl4-n wherein R is a chlorinated alkyl group containing two to 20 carbon atoms or a chlorinated cycloalkyl group containing three to 20 carbon atoms, and n is an integer of 1 to 4; (B) an aluminum component represented by the formula: AlR'm Cl3-m wherein R' is an alkyl group containing one to 10 carbon atoms, a cycloalkyl group containing three to 10 carbon atoms, or an aryl group, and m is 1.5 or 2; and (C) a coordinating component.
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